<PAGE>
                                                                    EXHIBIT 10.1

                       CLEAR CHANNEL COMMUNICATIONS, INC.

                                       AND

                              THE BANK OF NEW YORK,

                                   as Trustee

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

                        NINETEENTH SUPPLEMENTAL INDENTURE

                          Dated as of December 16, 2004

                                       TO

                                SENIOR INDENTURE

                           Dated as of October 1, 1997

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

                           5.50% Senior Notes due 2016

<PAGE>

                                                                               2

            Nineteenth Supplemental Indenture, dated as of the 16th day of
December 2004 (this "Nineteenth Supplemental Indenture"), between Clear Channel
Communications, Inc., a corporation duly organized and existing under the laws
of the State of Texas (hereinafter sometimes referred to as the "Company") and
The Bank of New York, a New York banking corporation, as trustee (hereinafter
sometimes referred to as the "Trustee") under the Indenture dated as of October
1, 1997, between the Company and the Trustee (the "Indenture"); as set forth in
Section 5.01 hereto and except as otherwise set forth herein, all terms used and
not defined herein are used as defined in the Indenture.

            WHEREAS, the Company executed and delivered the Indenture to the
Trustee to provide for the future issuance of its Securities, to be issued from
time to time in series as might be determined by the Company under the
Indenture, in an unlimited aggregate principal amount which may be authenticated
and delivered thereunder as in the Indenture provided;

            WHEREAS, pursuant to the terms of the Indenture, the Company desires
to provide for the establishment of a new series of its Securities to be known
as its 5.50% Senior Notes due 2016 (said series being hereinafter referred to as
the "Notes"), the form of such Notes and the terms, provisions and conditions
thereof to be as provided in the Indenture and this Nineteenth Supplemental
Indenture;

            WHEREAS, the Company desires and has requested the Trustee to join
with it in the execution and delivery of this Nineteenth Supplemental Indenture,
and all requirements necessary to make this Nineteenth Supplemental Indenture a
valid instrument, enforceable in accordance with its terms, and to make the
Notes, when executed by the Company and authenticated and delivered by the
Trustee, the valid obligations of the Company have been performed and fulfilled,
and the execution and delivery of this Supplemental Indenture and the Notes have
been in all respects duly authorized.

            NOW, THEREFORE, in consideration of the purchase and acceptance of
the Notes by the holders thereof, and for the purpose of setting forth, as
provided in the Indenture, the form of the Notes and the terms, provisions and
conditions thereof, the Company covenants and agrees with the Trustee as
follows:

                                    ARTICLE I

                    General Terms and Conditions of the Notes

            SECTION 1.01. (a) There shall be and is hereby authorized a series
of Securities designated the "5.50% Senior Notes due 2016", initially limited in
aggregate principal amount to $250,000,000. Without the consent of the Holders
of the Notes, the aggregate principal amount of the Notes, Notes may be
increased in the future, on the same terms and conditions and with the same
CUSIP number as the Notes. The Notes shall mature and the principal thereof
shall be due and payable, together with all accrued and unpaid interest thereon
on December 15, 2016.

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                                                                               3

            SECTION 1.02. The Notes shall be initially issued as Global
Securities. Principal and interest on the Notes issued in certificated form will
be payable, the transfer of such Notes will be registrable and such Notes will
be exchangeable for Notes, bearing identical terms and provisions at the office
or agency of the Company in the Borough of Manhattan, The City and State of New
York provided for that purpose and transfers of the Notes will also be
registrable at any of the Company's other offices or agencies as the Company may
maintain for that purpose; provided, however, that payment of interest may be
made at the option of the Company by check mailed to the registered holder at
such address as shall appear in the Security Register and that the payment of
principal with respect to the Notes will only be made upon surrender of the
applicable Notes to the Trustee.

            SECTION 1.03. Each Note will bear interest at the rate of 5.50% per
annum from December 16, 2004 until the principal thereof becomes due and
payable, payable (subject to the provisions of Article II) semi-annually in
arrears on June 15 and December 15 of each year (each, an "Interest Payment
Date", commencing on June 15, 2005), to the person in whose name such Note (or
one or more Predecessor Securities) are registered at the close of business on
the Regular Record Date for such interest installment, which, except as set
forth below, shall be June 1 or December 1 next preceding the Interest Payment
Date with respect to such interest installment. Any installment of interest not
punctually paid or duly provided for shall forthwith cease to be payable to the
registered holder of Notes on such Regular Record Date and may be paid to the
person in whose name such Notes (or one or more Predecessor Securities) are
registered at the close of business on a Special Record Date to be fixed by the
Trustee for the payment of such defaulted interest, notice whereof to be given
to the registered holders of the Notes, as applicable, not less than 10 days
prior to such Special Record Date, or may be paid at any time in any other
lawful manner not inconsistent with the requirements of any securities exchange
on which the Notes may be listed, and upon such notice as may be required by
such exchange, all as more fully provided in the Indenture.

            The amount of interest payable for any period will be computed on
the basis of a 360-day year consisting of twelve 30-day months. In the event
that any date on which interest is payable on the Notes is not a Business Day,
then payment of interest payable on such date will be made on the next
succeeding day which is a Business Day (and without any interest or other
payment in respect of any such delay).

            SECTION 1.04. The Notes are not entitled to any sinking fund.

            SECTION 1.05. Section 101 of the Indenture is hereby amended, solely
with respect to the Notes, by amending and restating the definition of
"Principal Property" as follows: "Principal Property" means any radio
broadcasting, television broadcasting, outdoor advertising or live entertainment
property located in the United States owned or leased by the Company or any
Subsidiary, unless, in the opinion of the Board of Directors of the Company,
such properties are not in the aggregate of material importance to the total
business conducted by the Company and its Subsidiaries as an entirety.

<PAGE>

                                                                               4

                                   ARTICLE II

                        Optional Redemption of the Notes

SECTION 2.01. The Notes will be redeemable as a whole at any time or in part
from time to time, at the option of the Company, at a redemption price equal to
the greater of (i) 100% of the principal amount of such Notes and (ii) the sum
of the present values of the remaining scheduled payments of principal and
interest thereon from the redemption date to December 15, 2016, discounted to
the redemption date on a semiannual basis (assuming a 360 day year consisting of
twelve 30-day months) at the Treasury Rate (as defined below) plus 30 basis
points, plus, in either case, any interest accrued but not paid to the date of
redemption. Notice of any redemption will be mailed at least 30 days but no more
than 60 days before the redemption date to each holder of the Notes to be
redeemed. Unless the Company defaults in payment of the redemption price, on and
after the redemption date interest will cease to accrue on the Notes or portions
thereof called for redemption. The Notes will not be subject to any sinking fund
provision.

            "Treasury Rate" means, with respect to any redemption date for the
Notes, (i) the yield, under the heading which represents the average for the
immediately preceding week, appearing in the most recently published statistical
release designated "H.15(519)" or any successor publication which is published
weekly by the Board of Governors of the Federal Reserve System and which
establishes yields on actively traded United States Treasury securities adjusted
to constant maturity under the caption "Treasury Constant Maturities," for the
maturity corresponding to the Comparable Treasury Issue (if no maturity is
within three months before or after the maturity date, yields for the two
published maturities most closely corresponding to the Comparable Treasury Issue
shall be determined and the Treasury Rate shall be interpolated or extrapolated
from such yields on a straight line basis, rounding to the nearest month), or
(ii) if such release referred to in clause (i) (or any successor release) is not
published during the week preceding the calculation date or does not contain the
yields referred to above, the rate per year equal to the semiannual equivalent
yield maturity of the Comparable Treasury Issue, calculated using a price for
the Comparable Treasury Issue (expressed as a percentage of its principal
amount) equal to the Comparable Treasury Price for such redemption date. The
Treasury Rate shall be calculated on the third Business Day preceding the
redemption date.

            "Comparable Treasury Issue" means the United States Treasury
security selected by an "Independent Investment Banker" as having a maturity
comparable to the remaining term of the Notes to be redeemed that would be
utilized, at the time of selection and in accordance with customary financial
practice, in pricing new issues of corporate debt securities of comparable
maturity to the remaining term of such Notes.

            "Independent Investment Banker" means, with respect to any
redemption date for the Notes, Banc of America Securities LLC and its successors
or, if such firm or any successor to such firm, as the case may be, is unwilling
or unable to select the Comparable Treasury Issue, an independent investment
banking institution of national standing appointed by the Trustee after
consultation with the Company.

<PAGE>

                                                                               5

            "Comparable Treasury Price" means, with respect to any redemption
date for the Notes, (i) the average of four Reference Treasury Dealer Quotations
(as defined below) for the redemption date, after excluding the highest and
lowest such Reference Treasury Dealer Quotations, or (ii) if the Trustee obtains
fewer than four such Reference Treasury Dealer Quotations, the average of all
such quotations obtained.

            "Reference Treasury Dealer" means Banc of America Securities LLC and
three other primary U.S. Government securities dealers in the United States
(each, a "Primary Treasury Dealer") appointed by the Trustee in consultation
with the Company. If any of the foregoing shall cease to be a Primary Treasury
Dealer, the Company shall substitute therefor another Primary Treasury Dealer.

            "Reference Treasury Dealer Quotations" means, with respect to each
Reference Treasury Dealer and any redemption date, the average, as determined by
the Trustee, of the bid and asked prices for the Comparable Treasury Issue
(expressed in each case as a percentage of its principal amount) quoted in
writing to the Trustee by such Reference Treasury Dealer at 5:00 p.m. on the
third Business Day preceding such redemption date.

                                   ARTICLE III

                                  Form of Notes

            SECTION 3.01. The Notes and the Trustee's Certificate of
Authentication to be endorsed thereon are to be substantially in the following
forms:

            UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE
OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION ("DTC"), TO THE ISSUER
OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY
CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS
IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC (AND ANY PAYMENT IS MADE TO
CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED
REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR
OTHERWISE BY OR TO ANY PERSON IS WRONGFUL SINCE THE REGISTERED OWNER HEREOF,
CEDE & CO., HAS AN INTEREST HEREIN.

            THIS SECURITY IS A GLOBAL SECURITY AS REFERRED TO IN THE INDENTURE
HEREINAFTER REFERENCED. UNLESS AND UNTIL IT IS EXCHANGED IN WHOLE OR IN PART FOR
THE INDIVIDUAL SECURITIES REPRESENTED HEREBY, THIS GLOBAL SECURITY MAY NOT BE
TRANSFERRED EXCEPT AS A WHOLE BY THE DEPOSITARY TO A NOMINEE OF THE DEPOSITARY
OR BY A NOMINEE OF THE DEPOSITARY TO THE DEPOSITARY OR ANOTHER NOMINEE OF THE
DEPOSITARY OR BY THE DEPOSITARY OR ANY SUCH NOMINEE TO A SUCCESSOR DEPOSITARY OR
A NOMINEE OF SUCH SUCCESSOR DEPOSITARY.

<PAGE>

                                                                               6

                       CLEAR CHANNEL COMMUNICATIONS, INC.
                     5.50% SENIOR NOTE DUE DECEMBER 15, 2016

REGISTERED                                                                  $[ ]

NO. R-[ ]                                                              CUSIP [ ]

                                                                        ISIN [ ]

            CLEAR CHANNEL COMMUNICATIONS, INC., a corporation duly organized and
existing under the laws of the State of Texas (herein called the "Company",
which term includes any successor under the Indenture hereinafter referred to),
for value received, hereby promises to pay to

                                   Cede & Co.

or registered assigns, the principal sum of $[ ] at the office or agency of the
Company in the Borough of Manhattan, The City of New York, on December 15, 2016
in such coin or currency of the United States of America as at the time of
payment shall be legal tender for the payment of public and private debts, and
to pay interest on said principal sum semiannually on June 15 and December 15 of
each year, commencing June 15, 2005 (each an "Interest Payment Date"), at said
office or agency, in like coin or currency, at the rate per annum specified in
the title hereof, from June 15 and December 15, as the case may be, next
preceding the date of this Note to which interest on the Notes has been paid or
duly provided for (unless the date hereof is the date to which interest on the
Notes has been paid or duly provided for, in which case from the date of this
Note), or if no interest has been paid on the Notes or duly provided for, from
December 16, 2004 until payment of said principal sum has been made or duly
provided for. Notwithstanding the foregoing, if the date hereof is after the 1st
day of any June or December and before the next succeeding June 15 and December
15, this Note shall bear interest from such June 15 or December 15, as the case
may be; provided, however, that if the Company shall default in the payment of
interest due on such June 15 or December 15, then this Note shall bear interest
from the next preceding June 15 or December 15 to which interest on the Notes
has been paid or duly provided for, or, if no interest has been paid on the
Notes or duly provided for, from December 16, 2004. The interest so payable, and
punctually paid or duly provided for, on any June 15 or December 15 will, except
as provided in the Indenture dated as of October 1, 1997, as supplemented to the
date of this Note (herein called the "Indenture"), duly executed and delivered
by the Company and The Bank of New York, as Trustee (herein called the
"Trustee"), be paid to the Person in whose name this Note (or one or more
Predecessor Securities) is registered at the close of business on the next
preceding June 1 or December 1, as the case may be (herein called the "Regular
Record Date"), whether or not a Business Day, and may, at the option of the
Company, be paid by check mailed to the registered address of such Person. Any
such interest which is payable, but is not so punctually paid or duly provided
for, shall forthwith cease to be payable to the registered Holder on such
Regular Record Date and may be paid either to the Person in whose name this Note
(or one or more Predecessor Securities) is registered at the close of business
on a Special Record Date for the payment of such

<PAGE>

                                                                               7

Defaulted Interest to be fixed by the Trustee, notice whereof shall be given to
Holders of the Notes not less than 10 days prior to such Special Record Date, or
may be paid at any time in any other lawful manner not inconsistent with the
requirements of any securities exchange on which the Notes may be listed and
upon such notice as may be required by such exchange, if such manner of payment
shall be deemed practical by the Trustee, all as more fully provided in the
Indenture. Notwithstanding the foregoing, in the case of interest payable at
Stated Maturity, such interest shall be paid to the same Person to whom the
principal hereof is payable. Interest on the Notes will be computed on the basis
of a 360-day year consisting of twelve 30-day months.

            The Bank of New York will be the Paying Agent and the Security
Registrar with respect to the Notes. The Company reserves the right at any time
to vary or terminate the appointment of any Paying Agent or Security Registrar,
to appoint additional or other Paying Agents and other Security Registrars which
may include the Company, and to approve any change in the office through which
any Paying Agent or Security Registrar acts; provided that there will at all
times be a Paying Agent in The City of New York and there will be no more than
one Security Registrar for the Notes.

            This Note is one of the duly authorized issue of debentures, notes,
bonds or other evidences of indebtedness (hereinafter called the "Securities")
of the Company, of the series hereinafter specified, all issued or to be issued
under and pursuant to the Indenture, to which Indenture and any other indentures
supplemental thereto reference is hereby made for a statement of the respective
rights, limitations of rights, obligations, duties and immunities thereunder of
the Trustee and any agent of the Trustee, any Paying Agent, the Company and the
Holders of the Securities and the terms upon which the Securities are issued and
are to be authenticated and delivered.

            The Securities may be issued in one or more series, which different
series may be issued in various aggregate principal amounts, may mature at
different times, may bear interest (if any) at different rates, may be subject
to different redemption provisions (if any), may be subject to different
covenants and Events of Default and may otherwise vary as provided or permitted
in the Indenture. This Note is one of the series of Securities of the Company
issued pursuant to the Indenture and designated as the 5.50% Senior Notes due
2016 (herein called the "Notes").

            The Notes will be redeemable as a whole at any time or in part from
time to time, at the option of the Company, at a redemption price equal to the
greater of (i) 100% of the principal amount of such Notes and (ii) the sum of
the present values of the remaining scheduled payments of principal and interest
thereon from the redemption date to December 15, 2016, discounted to the
redemption date on a semiannual basis (assuming a 360 day year consisting of
twelve 30-day months) at the Treasury Rate (as defined below) plus 30 basis
points, plus, in either case, any interest accrued but not paid to the date of
redemption. Notice of any redemption will be mailed at least 30 days but no more
than 60 days before the redemption date to each holder of the Notes to be
redeemed. Unless the Company defaults in payment of the redemption price, on and
after the redemption date interest will cease to accrue on the Notes or portions
thereof called for redemption. The Notes will not be subject to any sinking fund
provision.

<PAGE>

                                                                               8

            "Treasury Rate" means, with respect to any redemption date for the
Notes, (i) the yield, under the heading which represents the average for the
immediately preceding week, appearing in the most recently published statistical
release designated "H.15(519)" or any successor publication which is published
weekly by the Board of Governors of the Federal Reserve System and which
establishes yields on actively traded United States Treasury securities adjusted
to constant maturity under the caption "Treasury Constant Maturities," for the
maturity corresponding to the Comparable Treasury Issue (if no maturity is
within three months before or after the maturity date, yields for the two
published maturities most closely corresponding to the Comparable Treasury Issue
shall be determined and the Treasury Rate shall be interpolated or extrapolated
from such yields on a straight line basis, rounding to the nearest month), or
(ii) if such release referred to in clause (i) (or any successor release) is not
published during the week preceding the calculation date or does not contain the
yields referred to above, the rate per year equal to the semiannual equivalent
yield maturity of the Comparable Treasury Issue, calculated using a price for
the Comparable Treasury Issue (expressed as a percentage of its principal
amount) equal to the Comparable Treasury Price for such redemption date. The
Treasury Rate shall be calculated on the third Business Day preceding the
redemption date.

            "Comparable Treasury Issue" means the United States Treasury
security selected by an "Independent Investment Banker" as having a maturity
comparable to the remaining term of the Notes to be redeemed that would be
utilized, at the time of selection and in accordance with customary financial
practice, in pricing new issues of corporate debt securities of comparable
maturity to the remaining term of such Notes.

            "Independent Investment Banker" means, with respect to any
redemption date for the Notes, Banc of America Securities LLC, and its
successors or, if such firm or any successor to such firm, as the case may be,
is unwilling or unable to select the Comparable Treasury Issue, an independent
investment banking institution of national standing appointed by the Trustee
after consultation with the Company.

            "Comparable Treasury Price" means, with respect to any redemption
date for the Notes, (i) the average of four Reference Treasury Dealer Quotations
(as defined below) for the redemption date, after excluding the highest and
lowest such Reference Treasury Dealer Quotations, or (ii) if the Trustee obtains
fewer than four such Reference Treasury Dealer Quotations, the average of all
such quotations obtained.

            "Reference Treasury Dealer" means Banc of America Securities LLC and
three other primary U.S. Government securities dealers in the United States
(each, a "Primary Treasury Dealer") appointed by the Trustee in consultation
with the Company. If any of the foregoing shall cease to be a Primary Treasury
Dealer, the Company shall substitute therefor another Primary Treasury Dealer.

            "Reference Treasury Dealer Quotations" means, with respect to each
Reference Treasury Dealer and any redemption date, the average, as determined by
the Trustee, of the bid and asked prices for the Comparable Treasury Issue
(expressed in each case as a percentage of its principal amount) quoted in
writing to the Trustee by such

<PAGE>

                                                                               9

Reference Treasury Dealer at 5:00 p.m. on the third Business Day preceding such
redemption date.

            If an Event of Default with respect to the Notes shall occur and be
continuing, the principal of all of the Notes may be declared due and payable in
the manner, with the effect and subject to the conditions provided in the
Indenture.

            The Indenture permits, with certain exceptions as therein provided,
the Company and the Trustee to enter into supplemental indentures to the
Indenture for the purpose of adding any provisions to or changing in any manner
or eliminating any of the provisions of the Indenture or of modifying in any
manner the rights of the Holders of the Securities of each series under the
Indenture with the consent of the Holders of not less than a majority in
principal amount of the Securities at the time Outstanding of each series to be
affected thereby on behalf of the Holders of all Securities of such series, to
waive compliance by the Company with certain provisions of the Indenture and
certain past defaults and their consequences with respect to such series under
the Indenture. Any such consent or waiver by the Holder of this Note shall be
conclusive and binding upon such Holder and upon all future Holders of this Note
and of any Note issued upon the registration of transfer hereof or in exchange
here for or in lieu hereof, whether or not notation of such consent or waiver is
made upon this Note or such other Notes.

            No reference herein to the Indenture and no provision of this Note
or of the Indenture shall alter or impair the obligation of the Company, which
is absolute and unconditional, to pay the principal of and interest on this Note
at the place, rate and respective times and in the coin or currency herein and
in the Indenture prescribed.

            As provided in the Indenture and subject to the satisfaction of
certain conditions therein set forth, including the deposit of certain trust
funds in trust, the Company shall be deemed to have paid and discharged the
entire indebtedness represented by, and the obligations under, the Securities of
any series and to have satisfied all the obligations (with certain exceptions)
under the Indenture relating to the Securities of such series.

            The Notes are issuable in registered form without coupons in
denominations of $1,000 and any integral multiple of $1,000. Notes may be
exchanged for a like aggregate principal amount of Notes of other authorized
denominations at the office or agency of the Company in the Borough of
Manhattan, The City of New York, designated for such purpose or at any of the
Company's other offices or agencies as the Company may maintain for such purpose
and in the manner and subject to the limitations provided in the Indenture.

            Upon due presentment for registration of transfer of this Note at
the office or agency of the Company in the Borough of Manhattan, The City of New
York designated for such purpose or at any of the Company's other offices or
agencies as the Company may maintain for such purpose, a new Note or Notes of
authorized denominations for a like aggregate principal amount will be issued to
the transferee in exchange therefor, subject to the limitations provided in the
Indenture.

<PAGE>

                                                                              10

            No charge shall be made for any such transfer or exchange, but the
Company may require payment of a sum sufficient to cover any tax or other
governmental charge imposed in connection therewith.

            The Company, the Trustee and any agent of the Company or the Trustee
may treat the Person in whose name this Note is registered as the owner hereof
for all purposes, whether or not this Note is overdue, and neither the Company,
the Trustee nor any such agent shall be affected by notice to the contrary.

            Unless otherwise defined herein, all terms used in this Note which
are defined in the Indenture shall have the meanings assigned to them in the
Indenture.

            This Note shall be construed in accordance with and governed by the
laws of the State of New York.

            Unless the certificate of authentication hereon has been manually
executed by or on behalf of the Trustee under the Indenture, this Note shall not
be entitled to any benefits under the Indenture, or be valid or obligatory for
any purpose.

<PAGE>

                                                                              11

            IN WITNESS WHEREOF, CLEAR CHANNEL COMMUNICATIONS, INC. has caused
this Note to be duly executed.

                                       CLEAR CHANNEL COMMUNICATIONS, INC.

                                       by ______________________________________
                                             Name:
                                             Title:

[Company Seal]                         by ______________________________________
                                             Name:
                                             Title:

                     TRUSTEE'S CERTIFICATE OF AUTHENTICATION

            This is one of the Securities of the series designated therein
referred to in the within-mentioned Indenture.

                                       THE BANK OF NEW YORK,
                                           as Trustee,

Dated: _____________                   by ______________________________________
                                                  Authorized Signatory

<PAGE>

                                                                              12

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

                                  ABBREVIATIONS

            The following abbreviations, when used in the inscription on the
face of this instrument, shall be construed as though they were written out in
full according to applicable laws or regulations:

      TEN COM--as tenants in common

      TEN ENT--as tenants by the entireties

      JT TEN--as joint tenants with right of survivorship and not as tenants in
      common

      UNIF GIFT MIN ACT--...........Custodian.........

                                          (Cust)            (Minor)
                                Under Uniform Gifts to Minors Act
                                ----------------------------------
                                             (State)

                    Additional abbreviations may also be used
                          though not in the above list.

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

            FOR VALUE RECEIVED, the undersigned hereby sell(s), assign(s), and
transfer(s) unto

___________________________________
:                                              :
:__________________________________:
PLEASE INSERT SOCIAL SECURITY OR
OTHER IDENTIFYING NUMBER OF ASSIGNEE:

PLEASE PRINT OR TYPEWRITE NAME AND ADDRESS INCLUDING POSTAL ZIP CODE OF
ASSIGNEE:

________________________________________________________

<PAGE>

                                                                              13

__________________________________________________ the within Note and all
rights thereunder, hereby irrevocably constituting and appointing
______________________________ attorney to transfer said Note on the books of
the Company, with full power of substitution in the premises.

Dated: _______________________             _____________________________________
                                           Signature Guaranty
______________________________________
               Signature

(Signature must correspond with the        Signatures must be guaranteed by an
name as written upon the face of the       "eligible guarantor institution"
within instrument in every particular,     meeting the requirements of the
without alteration or enlargement or       Registrar, which requirements include
any change whatever.)                      membership or participation in the
                                           Security Transfer Agent Medallion
                                           Program ("STAMP") or such other
                                           "signature guarantee program" as may
                                           be determined by the Registrar in
                                           addition to, or in substitution for,
                                           STAMP, all in accordance with the
                                           Securities Exchange Act of 1934, as
                                           amended.

<PAGE>

                                                                              14

                                   ARTICLE IV

                             Original Issue of Notes

            SECTION 4.01. Notes in the aggregate principal amount equal to
$250,000,000 may, upon execution of this Nineteenth Supplemental Indenture, be
executed by the Company and delivered to the Trustee for authentication, and the
Trustee shall thereupon authenticate and make available for delivery said Notes
to or upon a Company Order.

                                    ARTICLE V

                            Miscellaneous Provisions

            SECTION 5.01. Except as otherwise expressly provided in this
Nineteenth Supplemental Indenture or in the forms of the Notes or otherwise
clearly required by the context hereof or thereof, all terms used herein or in
said forms of the Notes that are defined in the Indenture shall have the several
meanings respectively assigned to them thereby.

            SECTION 5.02. The Indenture, as supplemented by this Nineteenth
Supplemental Indenture, is in all respects ratified and confirmed. This
Nineteenth Supplemental Indenture shall be deemed part of the Indenture in the
manner and to the extent herein and therein provided.

            SECTION 5.03. The recitals herein contained are made by the Company
and not by the Trustee, and the Trustee assumes no responsibility for the
correctness thereof. The Trustee makes no representation as to the validity or
sufficiency of this Nineteenth Supplemental Indenture.

            SECTION 5.04. This Nineteenth Supplemental Indenture may be executed
in any number of counterparts each of which shall be an original; but such
counterparts shall together constitute but one and the same instrument.

<PAGE>

                                                                              15

            IN WITNESS WHEREOF, the parties hereto have caused this Nineteenth
Supplemental Indenture to be duly executed as of the day and year first above
written.

                                    CLEAR CHANNEL COMMUNICATIONS, INC.

                                    by:    /s/ Mark P. Mays
                                        ----------------------------------------
                                           Name: Mark P. Mays
                                           Title: President and Chief Executive
                                                  Officer

                                    THE BANK OF NEW YORK, as Trustee

                                    by:    /s/ Van K. Brown
                                        ----------------------------------------
                                           Name: Van K. Brown
                                           Title: Vice President