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                                                                  EXHIBIT 4.14.2

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                               AMFM OPERATING INC.


                                   AS OBLIGOR



                                       AND



                       U.S. TRUST COMPANY OF TEXAS, N.A.,


                                   AS TRUSTEE


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



                          FIRST SUPPLEMENTAL INDENTURE

                          DATED AS OF NOVEMBER 19, 1999

                                       TO

                                    INDENTURE


                            DATED AS OF JUNE 17, 1997


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



                                  $200,000,000

               9 1/4% SENIOR SUBORDINATED NOTES DUE 2007, SERIES A
               9 1/4% SENIOR SUBORDINATED NOTES DUE 2007, SERIES B


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         FIRST SUPPLEMENTAL INDENTURE dated as of November 19, 1999, among AMFM
OPERATING INC., a Delaware corporation (formerly Capstar Communications, Inc.,
the "Company") and U.S. TRUST COMPANY OF TEXAS, N.A., a national banking
association, as Trustee (the "Trustee").

         WHEREAS, Capstar Radio Broadcasting Partners, Inc. ("Capstar Radio")
has heretofore executed and delivered to the Trustee an Indenture dated as of
June 17, 1997 (the "Indenture"), providing for the issuance of $200,000,000
aggregate principal amount of 9-1/4% Senior Subordinated Notes due 2007, Series
A, and 9-1/4% Senior Subordinated Notes due 2007, Series B (collectively, the
"Notes");

         WHEREAS, pursuant to that certain Agreement and Plan of Merger by and
among Chancellor Media Corporation of Los Angeles ("CMCLA"), Capstar Radio, SBI
Holding Corporation ("SBI"), and the Company, dated as of November 19, 1999 (the
"Merger Agreement"), among other things, CMCLA, Capstar Radio, and SBI merged
with and into the Company (the "Merger");

         WHEREAS, the Company and the Trustee desire by this First Supplemental
Indenture pursuant to and as contemplated by Section 5.01(a)(1)(B) of the
Indenture, that the Company expressly assume all of the obligations under the
Notes and the Indenture;

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

         WHEREAS, all conditions and requirements necessary to make this First
Supplemental Indenture a valid, binding 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, for the benefit of the others and for the equal and ratable benefit of
the holders of the Notes, as follows:

                                    ARTICLE I

                       ASSUMPTION OF OBLIGATIONS AS ISSUER

         Section 1.01 ASSUMPTION. The Company hereby expressly and
unconditionally assumes each and every covenant, agreement and undertaking of
Capstar Radio under the Indenture as of the date of this First Supplemental
Indenture, and also hereby expressly and unconditionally assumes each and every
covenant, agreement and undertaking of Capstar Radio under each Note outstanding
on the date of this First Supplemental Indenture.




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                                   ARTICLE II

                            MISCELLANEOUS PROVISIONS

         Section 2.01 DEFINED TERMS. For all purposes of this First Supplemental
Indenture, except as otherwise defined or unless the context otherwise requires,
terms used in capitalized form in this First Supplemental Indenture and defined
in the Indenture have the meanings specified in the Indenture.

         Section 2.02 INDENTURE. Except as amended hereby, the Indenture and the
Notes are in all respects ratified and confirmed and all the terms shall remain
in full force and effect.

         Section 2.03 GOVERNING LAW. THIS FIRST SUPPLEMENTAL INDENTURE SHALL BE
GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK,
AS APPLIED TO CONTRACTS MADE AND PERFORMED WITHIN THE STATE OF NEW YORK, WITHOUT
REGARD TO PRINCIPLES OF CONFLICT OF LAWS.

         Section 2.04 SUCCESSORS. All agreements of the Company in this First
Supplemental Indenture and the Notes shall bind its successors. All agreements
of the Trustee in this First Supplemental Indenture shall bind its successors.

         Section 2.05 DUPLICATE ORIGINALS. All parties may sign any number of
copies of this First Supplemental Indenture. Each signed copy shall be an
original, but all of them together shall represent the same agreement.

         Section 2.06 SEVERABILITY. In case any one or more of the provisions in
this First Supplemental Indenture or in the Notes shall be held invalid, illegal
or unenforceable, in any respect for any reason, the validity, legality and
enforceability of any such provision in every other respect and of the remaining
provisions shall not in any way be affected or impaired thereby, it being
intended that all of the provisions hereof shall be enforceable to the full
extent permitted by law.

         Section 2.07 TRUSTEE DISCLAIMER. The Trustee accepts the amendment of
the Indenture effected by this First Supplemental Indenture and agrees to
execute the trust created by the Indenture as hereby amended, but on the terms
and conditions set forth in the Indenture, including the terms and provisions
defining and limiting the liabilities and responsibilities of the Trustee, which
terms and provisions shall in like manner define and limit its liabilities and
responsibilities in the performance of the trust created by the Indenture as
hereby amended, and without limiting the generality of the foregoing, the
Trustee shall not be responsible in any manner whatsoever for or with respect to
any of the recitals or statements contained herein, all of which recitals or
statements are made solely by the Company, or for or with respect to (i) the
validity or sufficiency of this First Supplemental Indenture or any of the terms
or provisions hereof, (ii) the proper authorization hereof by the Company by
corporate action or otherwise, (iii) the due execution hereof by the Company or


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(iv) the consequences (direct or indirect and whether deliberate or inadvertent)
of any amendment herein provided for, and the Trustee makes no representation
with respect to any such matters.

         Section 2.08 EFFECTIVENESS. This First Supplemental Indenture shall
become effective, once executed, upon receipt by the Trustee of a certificate of
the appropriate officers of the Company; and an opinion of Vinson & Elkins
L.L.P., counsel to the Company, each of which shall be dated no earlier than the
date hereof.

            [THE REMAINDER OF THIS PAGE IS INTENTIONALLY LEFT BLANK]



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

                                        AMFM OPERATING INC.,
                                        as Obligor


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

Attest:  /s/ Jean Menke
       -----------------------------

                                        U.S. TRUST COMPANY OF TEXAS, N.A.,
                                        as Trustee


                                         /s/ Bill Barber
                                        ---------------------------------------
                                        By:  Bill Barber
                                           ------------------------------------
                                        Title:  Vice President
                                              ---------------------------------

Attest:  /s/ Peg Makowski
       -----------------------------



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