QuickLinks -- Click here to rapidly navigate through this document

Exhibit 10.16

FIRST AMENDMENT TO ASSET PURCHASE AGREEMENT

        THIS FIRST AMENDMENT TO ASSET PURCHASE AGREEMENT (this "Amendment"), is
made as of January 9th, 2003, by and among BIG CITY RADIO, INC., a Delaware
corporation ("BCR"), BIG CITY RADIO-CHI, L.L.C., a Delaware limited liability
company ("BCR License Sub"; BCR, together with BCR License Sub, "Seller"), and
HBC ILLINOIS, INC., a Delaware corporation ("Purchaser").

        WHEREAS, Seller and Purchaser are parties to that certain Asset Purchase
Agreement dated as of January 2, 2003 (the "Purchase Agreement"), pursuant to
which Purchaser will acquire from Seller the Purchased Assets and Purchaser will
assume the obligations of Seller under the Assumed Contract, all subject to the
terms and conditions set forth in the Purchase Agreement;

        WHEREAS, simultaneously with the execution and delivery of this
Amendment, BCR License Sub and Purchaser are entering into a Time Brokerage
Agreement pursuant to which BCR License Sub will retain Purchaser to provide
programming and related services for the Station;

        WHEREAS, in connection with the execution and delivery of the Time
Brokerage Agreement, Purchaser and Seller desire to make certain modifications
to the Purchase Agreement; and

        WHEREAS, all capitalized terms used herein and not otherwise defined
herein shall have the meanings ascribed to such terms in the Purchase Agreement.

        NOW, THEREFORE, in consideration of the premises and the mutual
covenants and agreements herein contained, the parties hereto agree as follows:

        1.    Section 3.5.1, Section 3.5.2 and Section 3.5.3 of the Purchase
Agreement are hereby amended by adding the phrase "Subject to the terms and
conditions of the Time Brokerage Agreement" at the beginning of the first
sentence of each such Section.

        2.    Section 6.6 of the Purchase Agreement is hereby amended by adding
the phrase "Subject to the terms and conditions of the Time Brokerage Agreement
and the obligations of the parties thereunder" at the beginning of the first
sentence of such Section.

        3.    Section 6.7 of the Purchase Agreement is hereby amended by adding
the phrase ", except as contemplated by the Time Brokerage Agreement" at the end
of such Section.

        4.    Article 6 of the Purchase Agreement is hereby amended by adding
Section 6.10, the text of which reads as follows:

        "6.10. Time Brokerage Agreement.

        Notwithstanding anything to the contrary contained in this Agreement or
otherwise, Seller shall not be deemed to have breached or failed to comply with
any representations, warranties, covenants, or agreements with respect to the
Station or the Purchased Assets if such breach or failure is due or caused
directly by any act, omission or instruction of Purchaser under or in connection
with the Time Brokerage Agreement or any activities or transactions by Purchaser
in furtherance thereof or in connection therewith or any actions of Seller in
accordance with the terms of the Time Brokerage Agreement (except for such
actions of Seller that constitute gross negligence or willful misconduct)."

        5.    Section 10.1 of the Purchase Agreement is hereby amended by adding
Section 10.1.5 and Section 10.1.6, the text of which read as follows:

        "10.1.5. by Seller if Purchaser is in breach of its obligations under
the Time Brokerage Agreement, and (a) in the case of a breach by Purchaser
thereunder to pay money to Seller, such breach has not been cured by Purchaser
within five (5) days of written notice of such breach; and (b) in the case of
any other breach by Purchaser thereunder, such breach has not been cured by
Purchaser within thirty (30) days of written notice of such breach (or such
longer period of time if

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

the breach cannot be reasonably cured within thirty (30) days and Purchaser is
diligently attempting to cure such breach); or

        10.1.6. by Purchaser if Seller is in material breach of its obligations
under the Time Brokerage Agreement, and such breach has not been cured by Seller
within thirty (30) days of written notice of such breach (or such longer period
of time if the breach cannot be reasonably cured within thirty (30) days and
Seller is diligently attempting to cure such breach)."

        6.    Annex I of the Purchase Agreement is hereby amended by adding the
definition for "Time Brokerage Agreement", the text of which reads as follows:

        "Time Brokerage Agreement" shall mean the Time Brokerage Agreement
between BCR License Sub and Purchaser dated as of January 10, 2003."

        7.    Except as expressly modified hereby, all other terms and
conditions of the Purchase Agreement shall remain in full force and effect in
accordance with their terms.

        8.    This Amendment may be executed in one or more counterparts, each
of which will be deemed an original and all of which together will constitute
one and the same instrument.

        [The remainder of this page intentionally left blank.]

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

        IN WITNESS WHEREOF, each of the parties hereto has caused this First
Amendment to Asset Purchase Agreement to be executed as of the date first
written above.

    BIG CITY RADIO, INC.
 
 
By:
/s/  THOMAS E. REPKE      

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

    Name: Thomas E. Repke

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

    Title: Executive Vice President,
General Counsel and Secretary

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

 
 
BIG CITY RADIO-CHI, L.L.C.     By: BIG CITY RADIO, INC.,
Its Managing Member
 
 
By:
/s/  THOMAS E. REPKE      

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

    Name: Thomas E. Repke

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

    Title: Executive Vice President,
General Counsel and Secretary

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

 
 
HBC ILLINOIS, INC.
 
 
By:
       

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

    Name:        

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

    Title:        

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

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

QuickLinks

Exhibit 10.16

FIRST AMENDMENT TO ASSET PURCHASE AGREEMENT