Document:

<PAGE>   1
                                                                 EXHIBIT 4.16.14

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                          CAPSTAR COMMUNICATIONS, INC.
                        (formerly SFX Broadcasting, Inc.)

                                   as Issuer,

                                 THE GUARANTORS

                                       and

                            THE CHASE MANHATTAN BANK

                                   as Trustee

                         ------------------------------

                        THIRTEENTH SUPPLEMENTAL INDENTURE

                          Dated as of November 12, 1999

                                       to

                                    INDENTURE

                            Dated as of May 31, 1996

                         ------------------------------

                        10 3/4% SENIOR SUBORDINATED NOTES

                                    DUE 2006

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<PAGE>   2

                        THIRTEENTH SUPPLEMENTAL INDENTURE

         THIRTEENTH SUPPLEMENTAL INDENTURE, dated as of November 12, 1999, by
and among Capstar Communications, Inc., a Delaware corporation (the "Company");
and Capstar Communications California, Inc., a Delaware corporation; Liberty
Broadcasting of Albany Incorporated, a New York corporation; Liberty
Broadcasting of New York, Inc., a New York corporation; Parker Broadcasting
Company, a California corporation; WBAB, Inc., a New York corporation; WBLI,
Inc., a New York corporation; WGBB, Inc., a New York corporation; WGNA, Inc., a
New York corporation; WGNA-FM, Inc., a New York corporation; WHFM, Inc., a New
York corporation; WHJJ, Inc., a Rhode Island corporation; WHJY, Inc., a Rhode
Island corporation; WPYX, Inc., a New York corporation; WSNE, Inc., a Rhode
Island corporation; and WTRY, Inc., a New York corporation (each a "Guarantor");
and Capstar Radio Operating Company, a Delaware corporation; and Capstar TX
Limited Partnership, a Delaware limited partnership (together, the "New
Guarantors"); and The Chase Manhattan Bank, as trustee under the indenture
referred to below (the "Trustee").

                                 R E C I T A L S

         WHEREAS, the Company and the Guarantors have heretofore executed and
delivered to the Trustee an Indenture dated as of May 31, 1996 (the
"Indenture"), providing for the issuance of an aggregate principal amount of
$450,000,000 of 10 3/4% Senior Subordinated Notes due 2006 (the "Notes");

         WHEREAS, the Company, the Guarantors, the New Guarantors and the
Trustee desire by this Thirteenth Supplemental Indenture, pursuant to and as
contemplated by Sections 9.01 and 9.02 of the Indenture, to amend certain
provisions therein;

         WHEREAS, Section 4.15 of the Indenture provides that under certain
circumstances the Company is required to cause the New Guarantors to execute and
deliver to the Trustee a supplemental indenture pursuant to which the New
Guarantors shall unconditionally guarantee all of the Company's Obligations
under the Notes pursuant to a Subsidiary Guarantee on the terms and conditions
set forth herein;

         WHEREAS, the execution and delivery of this Thirteenth Supplemental
Indenture has been authorized by resolutions of the Boards of Directors of the
Company, the Guarantors and the New Guarantors;

         WHEREAS, the Company has requested that the holders of the Notes
consent to and approve the amendments set forth herein;

                                        1

<PAGE>   3

         WHEREAS, the Company has received written consents to such amendments
from holders of at least seventy-five percent (75%) in aggregate principal
amount of the Notes outstanding; and

         WHEREAS, all conditions and requirements necessary to make this
Thirteenth Supplemental Indenture a valid, binding and legal instrument in
accordance with its terms have been performed and fulfilled by the parties
hereto and the execution and delivery thereof have been in all respects duly
authorized by the parties hereto.

         NOW THEREFORE, in consideration of the above premises each party agrees
as follows for the benefit of each other and for the equal and ratable benefit
of the holders of the Notes:

                                   ARTICLE ONE

                    DEFINITIONS AND OTHER GENERAL PROVISIONS

         Section 1.1. Capitalized Terms. Each capitalized term used herein
without definition shall have the meaning assigned to such term in the
Indenture.

         Section 1.2. Effectiveness. This Thirteenth Supplemental Indenture
shall be effective upon execution by the parties hereto.

         Section 1.3. Incorporation of Thirteenth Supplemental Indenture into
Indenture. This Thirteenth Supplemental Indenture is executed by the Company,
the Guarantors, the New Guarantors and the Trustee pursuant to the provisions of
Sections 4.15, 9.01 and 9.02 of the Indenture, and the terms and conditions
hereof shall be deemed to be part of the Indenture for all purposes upon the
effectiveness of this Thirteenth Supplemental Indenture. The Indenture, as
amended and supplemented by this Thirteenth Supplemental Indenture, is in all
respects hereby adopted, ratified and confirmed.

         Section 1.4. Effect of Headings. The Articles and Section Headings
herein are for convenience only and shall not affect the construction hereof.

         Section 1.5. Governing Law. The internal law of the state of New York
shall govern and be used to construe this Thirteenth Supplemental Indenture.

         Section 1.6. Counterparts. This Thirteenth Supplemental Indenture may
be executed in any number of counterparts, each of which so executed shall be
deemed to be an original, but all such counterparts shall together constitute
but one and the same instrument.

         Section 1.7. Recitals. The recitals contained herein shall be taken as
the statements of the Company, the Guarantors and the New Guarantors and the
Trustee assumes no responsibility

                                       2

<PAGE>   4

for their correctness. The Trustee makes no representations as to the validity
or sufficiency of this Thirteenth Supplemental Indenture.

                                   ARTICLE TWO

                             AMENDMENTS TO INDENTURE

         Section 2.1. (a) Section 1.01 of the Indenture is amended to delete the
following definitions in their entirety:

         "Acquired Debt"
         "Advertising Business"
         "Asset Sale"
         "Attributable Debt"
         "Broadcast Business"
         "Cash Equivalents"
         "Change of Control"
         "Commitment Letter"
         "Consolidated Cash Flow"
         "Consolidated Indebtedness"
         "Consolidated Interest Expense"
         "Consolidated Net Income"
         "Consolidated Net Worth"
         "Continuing Directors"
         "Dallas Disposition"
         "Debt to Cash Flow Ratio"
         "Disposition"
         "Disposition Debt"
         "Disqualified Stock"
         "Equity Interests"
         "Exchange Notes"
         "Existing Indebtedness"
         "Existing MMR Indebtedness"
         "Fair Market Value"
         "Houston Exchange"
         "Investments"
         "Louisville Disposition"
         "Management Termination Agreements"
         "Material Broadcast License"
         "MMR"
         "MMR Merger"
         "MMR Stations"
         "MMR Warrants"

                                        3

<PAGE>   5

         "Net Income"
         "Net Proceeds"
         "New Credit Agreement"
         "Permitted Disposition Amount"
         "Permitted Investments"
         "Permitted Liens"
         "Permitted Refinancing Debt"
         "Preferred Stock"
         "Preferred Stock Offering"
         "Principal"
         "Registration Rights Agreement"
         "Related Party"
         "Restricted Investment"
         "SCMC"
         "Series B Preferred Stock"
         "Series C Preferred Stock"
         "Series D Preferred Stock"
         "SFX Merger Company"
         "Shared Facilities Agreement"
         "Significant Subsidiary"
         "Washington Disposition"
         "Weighted Average Life to Maturity"
         "Wholly Owned Subsidiary"

         (b)      Section 1.02 of the Indenture is amended to delete the
following definitions in their entirety:

         "Affiliate Transaction"
         "Asset Sale Offer"
         "Calculation Date"
         "Change of Control Offer"
         "Change of Control Payment"
         "Change of Control Payment Date"
         "Excess Proceeds"
         "incur"
         "insolvent"
         "Offer Amount"
         "Offer Period"
         "Permitted Debt"
         "Purchase Date"
         "Restricted Payments"

                                        4

<PAGE>   6

         (c)      Section 1.01 of the Indenture is amended to delete the last
sentence of the definition of "Bank Facilities" in its entirety.

         (d)      The following definitions in Section 1.01 of the Indenture are
amended and restated in their entirety to read as follows:

                  "Company" means Capstar Communications, Inc. (f/k/a SFX
         Broadcasting, Inc.) until a successor replaces it pursuant to this
         Indenture and thereafter means such successor and also includes for the
         purposes of any provision contained herein and required by the TIA any
         other obligor on the Notes.

                  "Guarantor" means each of the Persons named as a Guarantor or
         New Guarantor in the preamble to this Thirteenth Supplemental Indenture
         and their respective successors and assigns.

         Section 2.2. The following Sections are deleted in their entirety:
3.09, 4.03, 4.04, 4.05, 4.06, 4.07, 4.08, 4.09, 4.10, 4.11, 4.12, 4.14, 4.15,
4.16, 4.17, 4.18, 4.19, 4.20, 11.01, 11.02, 11.03, 11.04, 11.05, 11.06, and
11.07.

         Section 2.3. Section 2.06(h)(ii) of the Indenture is amended to delete
the clause ", 3.09, 4.10, 4.14" in its entirety.

         Section 2.4. Section 3.01 of the Indenture is amended to delete the
second paragraph thereof in its entirety.

         Section 2.5. The first sentence of Section 3.03 is amended and restated
in its entirety to read as follows:

                  "At least 30 days but not more than 60 days before a
         redemption date, the Company shall mail or cause to be mailed, by first
         class mail, a notice of redemption to each Holder whose Notes are to be
         redeemed at its registered address."

         Section 2.6. Section 3.05 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 3.05. DEPOSIT OF REDEMPTION OR PURCHASE PRICE.

                  On or prior to 10:00 a.m. Eastern Time on the redemption date,
         the Company shall deposit with the Trustee or with the Paying Agent
         money sufficient to pay the redemption or purchase price of and accrued
         interest and Liquidated Damages, if any, on all Notes to be redeemed or
         purchased on that

                                        5

<PAGE>   7

         date. The Trustee or the Paying Agent shall promptly return to the
         Company any money deposited with the Trustee or the Paying Agent by the
         Company in excess of the amounts necessary to pay the redemption or
         purchase price of, and accrued interest and Liquidated Damages, if any,
         on all Notes to be redeemed or purchased.

                  If Notes called for redemption are paid or if the Company has
         deposited with the Trustee or Paying Agent money sufficient to pay the
         redemption or purchase price of, and unpaid and accrued interest and
         Liquidated Damages, if any, on all Notes to be redeemed or purchased,
         on and after the applicable redemption or purchase date, interest and
         Liquidated Damages, if any, ceases to accrue on the Notes or the
         portions of Notes called for redemption (regardless of whether
         certificates for such Notes are actually surrendered). If a Note is
         redeemed or purchased on or after an interest record date but on or
         prior to the related interest payment date, then any accrued and unpaid
         interest and Liquidated Damages, if any, shall be paid to the Person in
         whose name such Note was registered at the close of business on such
         record date. If any Note called for redemption shall not be so paid
         upon surrender for redemption or purchase because of the failure of the
         Company to comply with the preceding paragraph, interest shall be paid
         on the unpaid principal, from the redemption or purchase date until
         such principal is paid, and to the extent lawful on any interest or
         Liquidated Damages, if any, not paid on such unpaid principal, in each
         case, at the rate provided in the Notes and in Section 4.01 hereof."

         Section 2.7. Section 3.08 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 3.08. MANDATORY REDEMPTION.

                  The Company shall not be required to make mandatory redemption
         payments with respect to the Notes."

         Section 2.8. The first paragraph of Section 4.01 of the Indenture is
amended and restated in its entirety to read as follows:

                  "The Company shall pay or cause to be paid the principal of,
         premium, if any, and interest on the Notes on the dates and in the
         manner provided in the Notes. Principal, premium, if any, and interest
         shall be considered paid on the date due if the Paying Agent, if other
         than the Company, any Guarantor or any Affiliate thereof, holds as of
         10:00 a.m. Eastern Time on the due date money deposited by the Company
         in immediately available funds and designated for and sufficient to pay
         all principal, premium, if any, and interest then due. The Company
         shall pay all Liquidated Damages, if any, in the same manner and on

                                        6

<PAGE>   8

         the dates as set forth above and in the amounts set forth in the
         Registration Rights Agreement."

         Section 2.9. Section 4.13 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 4.13. CONTINUED EXISTENCE.

                  Subject to Article 5 hereof, the Company shall do or cause to
         be done all things necessary to preserve and keep in full force and
         effect (i) its corporate, partnership, limited liability company or
         other existence in accordance its organizational documents (as the same
         may be amended from time to time) and (ii) the rights (charter and
         statutory), licenses and franchises of the Company; provided, however,
         that the Company shall not be required to preserve any such right,
         license or franchise if its Board of Directors shall determine that the
         preservation thereof is no longer desirable in the conduct of the
         business of the Company and that the loss thereof is not adverse in any
         material respect to the Holders of the Notes."

         Section 2.10. Section 5.01 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 5.01. MERGER, CONSOLIDATION, OR SALE OF ASSETS.

                  The Company shall not consolidate or merge with or into
         (whether or not the Company is the surviving corporation), or sell,
         assign, transfer, lease, convey or otherwise dispose of all or
         substantially all of its properties or assets in one or more related
         transactions, to another corporation, Person or entity unless (i) the
         Company is the surviving entity or the entity or the Person formed by
         or surviving any such consolidation or merger (if other than the
         Company) or to which such sale, assignment, transfer, lease, conveyance
         or other disposition shall have been made is a corporation organized or
         existing under the laws of the United States, any state thereof or the
         District of Columbia; and (ii) the entity or Person formed by or
         surviving any such consolidation or merger (if other than the Company)
         or the entity or Person to which such sale, assignment, transfer,
         lease, conveyance or other disposition shall have been made assumes all
         of the Obligations of the Company under the Notes and this Indenture
         pursuant to a supplemental indenture in a form substantially similar to
         Exhibit D hereto."

                                        7

<PAGE>   9

         Section 2.11. Section 6.01 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 6.01. EVENTS OF DEFAULT.

                  Each of the following constitutes an "Event of Default":

                  (i)      a default for 30 days in the payment when due of
                  interest on, or Liquidated Damages, if any, with respect to,
                  the Notes (whether or not prohibited by Article 10 hereof);

                  (ii)     a default in payment when due of the principal of or
                  premium, if any, on the Notes (whether or not prohibited by
                  Article 10 hereof);

                  (iii)    [intentionally left blank];

                  (iv)     [intentionally left blank];

                  (v)      [intentionally left blank];

                  (vi)     [intentionally left blank];

                  (vii)    [intentionally left blank];

                  (viii)   the Company:

                           (a)      commences a voluntary case,

                           (b)      consents to the entry of an order for relief
                           against it in an involuntary case,

                           (c)      consents to the appointment of a Custodian
                           of it or for all or substantially all of its
                           property,

                           (d)      makes a general assignment for the benefit
                           of its creditors, or

                           (e)      generally is not paying its debts as they
                           become due; or

                  (ix)     a court of competent jurisdiction enters an order or
                  decree under any Bankruptcy Law that:

                           (a)      is for relief against the Company;

                                        8

<PAGE>   10

                           (b)      appoints a Custodian of the Company; or

                           (c)      orders the liquidation of the Company;

                           and the order or decree remains unstayed and in
                  effect for 60 consecutive days.

                           The term "Custodian" means any receiver, trustee,
                  assignee, liquidator or similar official under any Bankruptcy
                  Law.

                           An Event of Default shall not be deemed to have
                  occurred under clause (iv) of this Section 6.01 until the
                  Trustee notifies the Company, or the Holders of at least 25%
                  in principal amount of the then outstanding Notes notify the
                  Company and the Trustee, of the Default and the Company does
                  not cure the Default within 60 days after receipt of the
                  notice. The notice must specify the Default, demand that it be
                  remedied and state that the notice is a "Notice of Default."

                           In the case of any Event of Default pursuant to the
                  provisions of this Section 6.01 occurring by reason of any
                  action (or inaction) willfully taken (or not taken) by or on
                  behalf of the Company with the intention of avoiding payment
                  of the premium that the Company would have had to pay if the
                  Company then had elected to redeem the Notes pursuant to
                  Section 3.07 hereof, an equivalent premium shall also become
                  and be immediately due and payable to the extent permitted by
                  law upon the acceleration of the Notes, anything in this
                  Indenture or in the Notes to the contrary notwithstanding. If
                  an Event of Default occurs prior to May 15, 2001 by reason of
                  any willful action (or inaction) taken (or not taken) by or on
                  behalf of the Company with the intention of avoiding the
                  prohibition on redemption of the Notes prior to May 15, 2001,
                  then the premium payable for purposes of this paragraph for
                  each of the years beginning May 15 of the years set forth
                  below shall be as set forth in the following table expressed
                  as a percentage of the amount that would otherwise be due but
                  for the provisions of this sentence, plus accrued interest and
                  Liquidated Damages, if any, to the date of payment:

<TABLE>
<CAPTION>

YEAR                    PERCENTAGE
----                    ----------
<S>                     <C>
1996                    114.335%
1997                    112.543%
1998                    110.751%
1999                    108.959%
2000                    107.167%"
</TABLE>

                                        9

<PAGE>   11

         Section 2.12. Section 6.02 of the Indenture is amended to delete the
following sentence in its entirety:

                  "Notwithstanding the foregoing, if an Event of Default
         specified in clauses (viii) or (ix) of Section 6.01 hereof occurs with
         respect to the Company, any of its Significant Subsidiaries or any
         group of its Subsidiaries that, taken together, would constitute a
         Significant Subsidiary, such an amount shall ipso facto become and be
         immediately due and payable without any declaration or other act on the
         part of the Trustee or any Holder."

         Section 2.13. Section 8.03 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 8.03. COVENANT DEFEASANCE.

                  Upon the Company's exercise under Section 8.01 hereof of the
         option applicable to this Section 8.03, the Company and the Guarantors
         shall, subject to the satisfaction of the conditions set forth in
         Section 8.04 hereof, be released from their obligations under the
         covenants contained in Section 5.01 hereof with respect to the
         outstanding Notes on and after the date the conditions set forth below
         are satisfied (hereinafter, "Covenant Defeasance"), and the Notes shall
         thereafter be deemed not "outstanding" for the purposes of any
         direction, waiver, consent or declaration or act of Holders (and the
         consequences of any thereof) in connection with such covenants, but
         shall continue to be deemed "outstanding" for all other purposes
         hereunder (it being understood that such Notes shall not be deemed
         "outstanding" for accounting purposes). For this purpose, Covenant
         Defeasance means that, with respect to the outstanding Notes, the
         Company may omit to comply with and shall have no liability in respect
         of any term, condition or limitation set forth in any such covenant,
         whether directly or indirectly, by reason of any reference elsewhere
         herein to any such covenant or by reason of any reference in any such
         covenant to any other provision herein or in any other document, but,
         except as specified above, the remainder of this Indenture and such
         Notes shall be unaffected thereby. In addition, upon the Company's
         exercise under Section 8.01 hereof of the option applicable to this
         Section 8.03, subject to the satisfaction of the conditions set forth
         in Section 8.04 hereof, Sections 6.01(iv) through 6.01(ix) hereof shall
         not constitute Events of Default."

                                       10

<PAGE>   12

         Section 2.14. Section 9.02 of the Indenture is amended and restated in
its entirety to read as follows:

         "SECTION 9.02. WITH CONSENT OF HOLDERS OF NOTES.

                  The Company and the Trustee may amend or supplement this
         Indenture and the Notes may be amended or supplemented with the consent
         of the Holders of at least a majority in principal amount of the Notes
         then outstanding (including consents obtained in connection with a
         purchase of, or tender offer or exchange offer for the Notes), and,
         subject to Sections 6.04 and 6.07 hereof, any existing Default or Event
         of Default (other than a Default or Event of Default in the payment of
         the principal of, premium or Liquidated Damages, if any, or interest on
         the Notes) or compliance with any provision of this Indenture or the
         Notes may be waived with the consent of the Holders of a majority in
         principal amount of the then outstanding Notes (including consents
         obtained in connection with a purchase of, or tender offer or exchange
         offer for the Notes). Any amendment to the provisions of Article 10
         hereof will require the consent of the Holders of at least 75% in
         aggregate principal amount of the Notes then outstanding if such
         amendment would adversely affect the rights of Holders of Notes.

                  Upon the request of the Company accompanied by a resolution of
         the Board of Directors of the Company and each of the Guarantors
         authorizing the execution of any such amended or supplemental
         indenture, and upon the filing with the Trustee of evidence
         satisfactory to the Trustee of the consent of the Holders of Notes as
         aforesaid, and upon receipt by the Trustee of the documents described
         in Section 7.02 hereof, the Trustee shall join with the Company and
         each of the Guarantors in the execution of such amended or supplemental
         indenture unless such amended or supplemental indenture affects the
         Trustee's own rights, duties or immunities under this indenture or
         otherwise, in which case the Trustee may in its discretion, but shall
         not be obligated to, enter into such amended or supplemental indenture.

                  It shall not be necessary for the consent of the Holders of
         Notes under this Section 9.02 to approve the particular form of any
         proposed amendment or waiver, but it shall be sufficient if such
         consent approves the substance thereof. However, without the consent of
         each Holder, an amendment or waiver may not (with respect to any Notes
         held by a non-consenting Holder):

                           (a)      reduce the principal amount of Notes whose
                           Holders must consent to an amendment, supplement or
                           waiver;

                           (b)      reduce the principal of or change the fixed
                           maturity of any Note or alter or waive any of the
                           provisions with respect to the redemption of the
                           Notes;

                                       11

<PAGE>   13

                           (c)      reduce the rate of or change the time for
                           payment of interest, including default interest, on
                           any Note;

                           (d)      waive a Default or Event of Default in the
                           payment of principal of or premium or Liquidated
                           Damages, if any, or interest on the Notes (except a
                           rescission of acceleration of the Notes by the
                           Holders of at least a majority in aggregate principal
                           amount of the then outstanding Notes and a waiver of
                           the payment default that resulted from such
                           acceleration);

                           (e)      make any Note payable in money other than
                           that stated in the Notes;

                           (f)      make any change in the provisions of this
                           Indenture relating to waivers of past Defaults or the
                           rights of Holders of Notes to receive payments of
                           principal of or premium or Liquidated Damages, if
                           any, or interest on the Notes;

                           (g)      waive a redemption payment with respect to
                           any Note; or

                           (h)      make any change in Section 6.04 or 6.07
                           hereof or in the foregoing amendments and waiver
                           provisions."

         Section 2.15. Section 10.01 of the Indenture is amended to delete the
clause "and in Article 11" in its entirety.

                                  ARTICLE THREE

                             AGREEMENT TO GUARANTEE

         Section 3.1. The New Guarantors hereby agree, jointly and severally
with all other Guarantors, to guarantee the Company's obligations under the
Notes on the terms and subject to the conditions set forth in Article 11 of the
Indenture in the form existing immediately prior to the date hereof and to be
bound by all other applicable provisions of the Indenture, including, without
limitation, the provisions of Article 10 of the Indenture.

                  [Remainder of page intentionally left blank]

                                       12

<PAGE>   14

         IN WITNESS WHEREOF, the parties hereto have caused this THIRTEENTH
SUPPLEMENTAL INDENTURE to be duly executed as of the date first written above.

                                         THE CHASE MANHATTAN BANK,
                                         as Trustee
                                         By:    /s/ Francine Springer
                                               ---------------------------------
                                         Name:    Francine Springer
                                               ---------------------------------
                                         Title:    Assistant Vice President
                                               ---------------------------------

                                         CAPSTAR COMMUNICATIONS, INC.
                                         CAPSTAR COMMUNICATIONS
                                            CALIFORNIA, INC.
                                         CAPSTAR RADIO OPERATING
                                            COMPANY
                                         LIBERTY BROADCASTING OF
                                            ALBANY INCORPORATED
                                         LIBERTY BROADCASTING OF
                                            NEW YORK, INC.
                                         PARKER BROADCASTING COMPANY
                                         WBAB, INC.
                                         WBLI, INC.
                                         WGBB, INC.
                                         WGNA, INC.
                                         WGNA-FM, INC.
                                         WHFM, INC.
                                         WHJJ, INC.
                                         WHJY, INC.
                                         WPYX, INC.
                                         WSNE, INC.
                                         WTRY, INC.

                                         By:    /s/ W. Schuyler Hansen
                                               ---------------------------------
                                                  W. Schuyler Hansen
                                                  Senior Vice President and
                                                  Chief Accounting Officer

                                       S-1

<PAGE>   15

                                         CAPSTAR TX LIMITED PARTNERSHIP
                                         By: Capstar Radio Operating Company,
                                         its general partner

                                         By:    /s/ W. Schuyler Hansen
                                               ---------------------------------
                                                  W. Schuyler Hansen
                                                  Senior Vice President and
                                                  Chief Accounting Officer

                                      S-2<PAGE>   1
                                                                 EXHIBIT 10.10.2

                               FIRST AMENDMENT OF
                        THE CHANCELLOR MEDIA CORPORATION
                             1999 STOCK OPTION PLAN

                  This First Amendment of the Chancellor Media Stock Option Plan
(the "Plan") is made effective as of the 13th day of July, 1999 by AMFM Inc.
(formerly known as Chancellor Media Corporation), a Delaware corporation (the
"Company").

                  WHEREAS, each of the Board of Directors of the Company and the
stockholders of the Company have heretofore adopted and approved the Plan;

                  WHEREAS, as of the date hereof, the Company has changed its
name from Chancellor Media Corporation to AMFM Inc. pursuant to that certain
merger of July 13, 1999 (the "Merger") according to the Agreement and Plan of
Merger, dated as of August 26, 1998, and amended and restated as of April 29,
1999, by and among the Company, Capstar Broadcasting Corporation, a Delaware
corporation, CBC Acquisition Company, Inc., a Delaware corporation, and CMC
Merger Sub, Inc., a Delaware corporation and a wholly-owned subsidiary of the
Company;

                  WHEREAS, the Company desires to amend the Plan to change the
vesting schedule and term of options granted thereunder; and

                  NOW, THEREFORE, the Plan is amended as follows:

                  1.  TITLE OF PLAN.

                  The title of the Plan, as set forth on the first page of the
Plan, is hereby amended to read, in its entirety, as follows:

                        AMFM INC. 1999 STOCK OPTION PLAN

                  2.  SECTION 1.

                  The name of the Company in the first sentence of Section 1 is
amended to read "AMFM Inc."

                  3.  SECTION 6(c).

                  Section 6(c) is amended in its entirety as follows:

                  "Term. The term of each Option shall be established by the
Committee and set forth at the time the Option is granted. The term of the
Option shall not exceed 3 (three) years from the date of grant of such Option;
provided, however, that Options for up to an aggregate of 500,000 shares of
Common Stock may have terms exceeding three (3) years but not exceeding ten (10)
years if the Company was contractually committed as

<PAGE>   2

of July 1, 1999 to issue such Options with such terms exceeding three (3) years.
An Option may be terminated prior to the expiration of its term in accordance
with the provisions of the Plan."

                  4.  SECTION 6(d).

                  Section 6(d) is amended in its entirety as follows:

                  "Vesting and Exercisability. Unless otherwise determined by
the Committee, and subject to the provisions of subsection 6(e), (f), (g) and
(h) below, Options granted to any Key Employee or Eligible Non-Employee pursuant
to this Section 6 shall vest and become exercisable in accordance with and on
the dates described in the schedule set forth below; provided, however, that
unless otherwise determined by the Committee, such Options shall vest and become
exercisable on any such date only if such Key Employee or Eligible non-Employee
is employed or providing services to the Company or any Related Entity on such
date:

                  o        all of the shares of Common Stock underlying such
                           Option shall vest and become exercisable on the first
                           anniversary of the date of grant of such Option.

                  No Option by its terms shall be exercisable after the
expiration of three years from the date of grant of the Option; provided,
however, that in no event shall an optionee have less than 30 days to exercise
an option which has become vested."

                  5.       SECTION 7(c).

                  "Term. The term of each Value Option shall be established by
the Committee and set forth at the time the Option is granted. The term of the
Option shall not exceed 5 (five) years from the date of grant of such Option
except as provided in subsections 7(e), (f), (g), (h), and (i). An Option may be
terminated prior to the expiration of its term in accordance with the provisions
of the Plan."

                  6.       SECTION 7(e).

                  Section 7(e) is amended in its entirety as follows (which
amendment does not amend the terms or operation of the Exercisability Value (as
such term is defined in the Plan):

"e.               Exercisability. A Value Option granted on or prior to June 1,
                  1999 shall become exercisable after the date on which the
                  average Fair Market Value of a share of Common Stock,
                  calculated on a daily basis, equals or

                                       2

<PAGE>   3

                  exceeds $100.00 per share and a Value Option granted on or
                  after June 1, 1999 shall become exercisable after the date on
                  which the Average Fair Market Value of a share of Common
                  Stock, calculated on a daily basis, equals or exceeds the
                  greater of (i) $100.00 per share or (ii) two-hundred percent
                  (200%) of the exercise price for a share of Common Stock under
                  such Option (the "Exercisability Value"), for a period of 30
                  consecutive days (excluding non-business days for the purpose)
                  during the period from (and including) the date of grant of
                  such Option through (and including) the fifth anniversary of
                  the date of grant of such Option. No Value Option (whether or
                  not vested) shall become exercisable after 5:00 p.m., in
                  Dallas, Texas, on the fifth anniversary of the date of grant
                  of such Option, and any Value Option (whether or not vested)
                  that is not exercisable at such time shall automatically, and
                  without notice, terminate and become null and void at such
                  time and any Value Option that is exercisable at such time may
                  be exercised until the 90th day after such date. In addition,
                  the exercisability of a Value Option shall be subject to
                  subsections 7(f), (g), (h) and (i) and Section 9.

                  7.       SECTION 11.

                  Section 11 is amended in its entirety as follows:

                  "Assignment or Transfer. During the lifetime of an optionee,
Options shall be exercisable only by the optionee or by the optionee's legal
representative in the event that such a representative has been appointed in
connection with the Disability of the optionee. Except as otherwise expressly
provided in any Option, no Option granted under the Plan or any rights or
interests therein shall be assignable or transferable by an optionee except by
will or the laws of descent and distribution; provided, however, that any
optionee may, subject to the approval of the Compensation Committee of the
Board, have an Option issued directly in the name of, or assign or otherwise
transfer an Option to, a trust or limited partnership established for the
benefit of such optionee's spouse, siblings, parents, children and/or
grandchildren."

                  In all other respects, the Plan is ratified and confirmed.

                                                 AMFM INC. (formerly known as
                                                 CHANCELLOR MEDIA CORPORATION)

                                                 By:   /s/
                                                       ------------------------
                                                 Name:
                                                       ------------------------
                                                 Title:
                                                       ------------------------

                                       3

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