1 EXHIBIT 4(ff) THIRD AMENDMENT TO SECOND AMENDED AND RESTATED STOCKHOLDERS' AGREEMENT THIS THIRD AMENDMENT TO SECOND AMENDED AND RESTATED STOCKHOLDERS' AGREEMENT (this "Third Amendment") is made and entered into effective as of August 31, 1999, by and among Regent Communications, Inc. (as so amended, the "Company") and the undersigned stockholders (the "Stockholders"). W I T N E S S E T H: THAT, WHEREAS, the Company and the Stockholders are parties to a certain Second Amended and Restated Stockholders' Agreement dated as of June 15, 1998, as amended (as so amended, the "Stockholders' Agreement"); and WHEREAS, on the effective date hereof, The Roman Arch Fund L.P. and The Roman Arch Fund II L.P. (collectively, "The Roman Arch Funds") purchased shares of the Company's Series H Convertible Preferred Stock; and WHEREAS, it is in the best interests of the Company and the Stockholders that The Roman Arch Funds purchase such shares; and WHEREAS, as an inducement to The Roman Arch Funds to purchase such shares, the Company and the Stockholders are willing to cause the Stockholders' Agreement to be amended to add The Roman Arch Funds as parties to the Agreement. NOW, THEREFORE, in consideration of the premises and the agreements contained herein, it is agreed as follows: 1. AMENDMENT. The Stockholders' Agreement is hereby amended to add The Roman Arch Funds as parties thereto. 2. AGREEMENT TO BE BOUND. The Roman Arch Fund L.P. and The Roman Arch Fund II L.P., by their execution hereof, agree to be bound by all of the provisions of the Stockholders' Agreement, as amended. 3. TERMS OF AGREEMENT UNAFFECTED. The terms, conditions and provisions of Stockholders' Agreement remain in full force and effect. 4. COUNTERPARTS. This Third Amendment may be executed in any number of counterparts and by different parties hereto in separate counterparts, each of which when so executed and delivered shall be deemed an original, but all such counterparts together shall constitute but one and the same instrument. 2 IN WITNESS WHEREOF, the signatories below have caused this Amendment to be executed and delivered effective as of the date first above written. REGENT COMMUNICATIONS, INC. WALLER-SUTTON MEDIA PARTNERS, L.P. By: /s/ Terry S. Jacobs By: Waller-Sutton Media, L.L.C., ------------------------------ Its: Chairman & CEO Its: /s/ William H. Ingram, Chairman ------------------------------ ------------------------------- /s/ Terry S. Jacobs - ----------------------------------- TERRY S. JACOBS BLUE CHIP CAPITAL FUND II LIMITED PARTNERSHIP /s/ William L. Stakelin By: Blue Chip Venture Company, Ltd., - ----------------------------------- its General Partner WILLIAM L. STAKELIN /s/ Joel M. Fairman By: /s/ John H. Wyant - ----------------------------------- ----------------- JOEL M FAIRMAN Its: Manager -------- MIAMI VALLEY VENTURE FUND, L.P. PNC BANK, N.A., AS TRUSTEE By: Blue Chip Venture Company of Dayton, By: /s/ Louis E. Valker Ltd., its Special Limited Partner ------------------------------- Its: Vice President By: /s/ John H. Wyant ------------------------------- John H. Wyant, Manager WPG CORPORATE DEVELOPMENT RIVER CITIES CAPITAL FUND LIMITED ASSOCIATES V, L.L.C. PARTNERSHIP By: /s/ Kenneth J. Hanau By: /s/ R. Glen Mayfield ------------------------------ --------------------------------------- Its: Member Its: Vice President of Mayson, Inc., General ------------------------------ ----------------------------------------- Partner of River Cites Management Limited ----------------------------------------- Partnership, General Partner of River ----------------------------------------- Cities Capital Fund Limited Partnership ----------------------------------------- WPG CORPORATE DEVELOPMENT ASSOCIATES V (OVERSEAS), L.P. BMO FINANCIAL, INC. By: /s/ Kenneth J. Hanau By: Yvonne Bos --------------------------------- ----------------------------------------- Its: Member Its: Senior Vice President ------------------------------ ----------------------------------------- -2- 3 GENERAL ELECTRIC CAPITAL THE ROMAN ARCH FUND L.P. CORPORATION By: /s/ Robert Willard --------------------------------------- By: /s/ Kenneth M. Gacevich ------------------------------ Its: Executive Vice President -------------------------------------- Its: Duly Authorized Signatory ------------------------------ THE ROMAN ARCH FUND II L.P. By: /s/ Robert Willard ----------------------------------------- Its: Executive Vice President ----------------------------------------- /s/ William H. Ingram ------------------------------ WILLIAM H. INGRAM -3-