UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 13D

(Rule 13d-102)

INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT

TO RULE 13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO

RULE 13d-2(a)

(Amendment No. 5)*

Cumulus Media Inc.

(Name of Issuer)

Class A Common Stock, par value $0.01 per share

(Title of Class of Securities)

231082108

(CUSIP Number)

Ross A. Oliver, Esq.

Crestview Partners II GP, L.P.

667 Madison Avenue

New York, NY 10065

(212) 906-0700

(Name, Address and Telephone Number of Person

Authorized to Receive Notices and Communications)

December 6, 2016

(Date of Event which Requires Filing of this Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box ¨.

Note: Schedules filed in paper format shall include a signed original and five copies of the schedule, including all exhibits. See §240.13d-7 for other parties to whom copies are to be sent.

* The remainder of this cover page shall be filled out for a reporting person’s initial filing on this form with respect to the subject class of securities, and for any subsequent amendment containing information which would alter disclosures provided in a prior cover page.

The information required on the remainder of this cover page shall not be deemed to be “filed” for the purpose of Section 18 of the Securities Exchange Act of 1934 (the “Act”) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

CUSIP No. 231082108

SCHEDULE 13D

Pursuant to Rule 13d-2(a) of the General Rules and Regulations under the Exchange Act, the undersigned hereby amends the Schedule 13D originally filed on September 26, 2011, as amended by Amendment 1 thereto filed on November 22, 2011, Amendment 2 thereto filed on December 14, 2012, Amendment 3 thereto filed on April 29, 2015 and Amendment 4 thereto filed on November 25, 2015 (the “Schedule 13D”), relating to the Class A common stock, par value $0.01 per share (“Class A Common Stock”), of Cumulus Media Inc. (the “Issuer”).

Item 2. Identity and Background.

Item 2 of the Schedule 13D is hereby amended by deleting the first paragraph and replacing it with the following:

“The names of the persons filing this statement are Crestview Partners II GP, L.P. (“Crestview GP”), Crestview Radio Investors, LLC (“Crestview Radio Investors”), Crestview Partners II, L.P. (“DE Fund”), Crestview Partners II (TE), L.P. (“TE Fund”), Crestview Partners II (FF), L.P. (“FF Fund”), Crestview Offshore Holdings II (Cayman), L.P. (“Cayman Fund”), Crestview Offshore Holdings II (FF Cayman), L.P. (“FF Cayman Fund”), Crestview Offshore Holdings II (892 Cayman), L.P. (“892 Cayman Fund,” and together with DE Fund, TE Fund, FF Fund, Cayman Fund and FF Cayman Fund, the “Crestview Funds”) and Crestview Advisors, L.L.C. (“Crestview Advisors” and, together with Crestview Radio Investors, the Crestview Funds and Crestview GP, the “Reporting Persons” and each, a “Reporting Person”). Crestview GP serves as the general partner of the Crestview Funds. The general partner of Crestview GP is Crestview, L.L.C. Each of the Crestview Funds is a private investment fund and a member of Crestview Radio Investors, which is a special purpose investment vehicle. DE Fund, TE Fund, FF Fund, Cayman Fund, FF Cayman Fund and 892 Cayman Fund are 74.5%, 2.4%, 4.1%, 11.4%, 1.3% and 6.3% members, respectively, in Crestview Radio Investors, which is the record owner of 8,122,723 shares of Class A Common Stock and a warrant to purchase 976,944 shares of Class A Common Stock. Crestview Advisors provides investment advisory and management services to the Crestview Funds. The address of the principal office of each of the Reporting Persons and Crestview, L.L.C. is 667 Madison Avenue, New York, New York 10065.”

Item 3. Source and Amount of Funds or Other Consideration.

Item 3 of the Schedule 13D is hereby amended to add the following at the end of such section:

“On May 14, 2016, 40,486 restricted shares of Class A Common Stock held by Jeffrey Marcus and 40,486 restricted shares of Class A Common Stock held by Brian Cassidy, in each case that were granted by the Issuer on May 14, 2015 in respect of their service on the Board, became fully vested. Each of Mr. Marcus and Mr. Cassidy is a Partner of Crestview Advisors. In connection with the vesting of these securities, Messrs. Marcus and Cassidy assigned all rights, title and interest in these securities to Crestview Advisors.”

Item 4. Purpose of Transaction.

Item 4 of the Schedule 13D is hereby amended to add the following at the end of such section: 

On December 6, 2016, the Issuer, Cumulus Media Holdings Inc. (“Holdings”), a direct wholly-owned subsidiary of the Issuer, and certain other direct and indirect subsidiaries of Holdings entered into a refinancing support agreement (the “Refinancing Support Agreement”) with holders (the “Supporting Noteholders”) of approximately $349.7 million, or 57.3%, of the aggregate principal amount of the outstanding 7.75% Senior Notes due 2019 (the “Outstanding Notes”) issued by Holdings and guaranteed by the Issuer. The Refinancing Support Agreement sets forth the terms of a refinancing of the Outstanding Notes, and pursuant to its terms the Supporting Noteholders have agreed to tender their Outstanding Notes in a contemplated exchange offer (the “Exchange Offer”), subject to certain conditions set forth in the Refinancing Support Agreement.

In addition, on December 6, 2016, the Issuer and Crestview Radio Investors entered into a voting agreement pursuant to which Crestview Radio Investors agreed that at each annual, special or other meeting of the stockholders of the Issuer, or at any adjournment or postponement thereof, or in any other circumstances upon which a vote, consent or other approval of the Issuer’s stockholders is sought, in each case, with respect to (i) the issuance of shares of Class A Common Stock in the Exchange Offer and (ii) the amendment and restatement of the Issuer’s certificate of incorporation to increase the number of authorized shares of Class A Common Stock and effect the issuance of Class D common stock and Class E common stock to certain Supporting Noteholders (collectively, the “Transactions”), Crestview Radio Investors will (a) when a meeting is held, attend such meeting or otherwise cause such shares of common stock it holds to be counted as present thereat, and (b) vote (or cause to be voted) all shares of common stock held by Crestview Radio Investors as of the date of such meeting that are eligible to vote on the matter or matters submitted to a vote of the Issuer’s stockholders at such meeting in accordance with the recommendation of the Board with respect to the Transactions.

Item 5. Interest in Securities of the Issuer.

Item 5(a) of the Schedule 13D is hereby amended and restated in its entirety as follows: 

“(a) Amount beneficially owned:

As of December 6, 2016, the Reporting Persons beneficially owned in the aggregate 9,120,557 shares of the Class A Common Stock. Such shares constitute 30.20% of the outstanding shares of the Class A Common Stock, based on (i) 29,224,867 shares of Class A Common Stock outstanding as of November 1, 2016 as reported in the Issuer’s Quarterly Report filed on Form 10-Q with the Securities and Exchange Commission (“SEC”) on November 8, 2016, plus (ii) 976,944 shares of the Class A Common Stock, which may be acquired upon exercise of the Class A Warrant.

Crestview GP is the general partner of each of the Crestview Funds. Each of the Crestview Funds is a member of Crestview Radio Investors. DE Fund, TE Fund, FF Fund, Cayman Fund, FF Cayman Fund and 892 Cayman Fund are 74.5%, 2.4%, 4.1%, 11.4%, 1.3% and 6.3% members, respectively, in Crestview Radio Investors, which is the record owner of 8,122,723 shares of the Class A Common Stock and the Class A Warrant to purchase 976,944 shares of the Class A Common Stock.

Crestview Advisors owns 20,890 shares of Class A Common Stock.

Crestview GP may be deemed to beneficially own the 20,890 shares of Class A Common Stock owned by Crestview Advisors.

Each Reporting Person disclaims beneficial ownership of the reported securities except and to the extent of its pecuniary interest therein.

(b) Number of shares as to which such person has:

(i) Sole power to vote or direct the vote:

See item 7 on Cover Pages to this Schedule 13D.

(ii) Shared power to vote or to direct the vote:

See item 8 on Cover Pages to this Schedule 13D.

(iii) Sole power to dispose or to direct the disposition of:

See item 9 on Cover Pages to this Schedule 13D.

(iv) Shared power to dispose or to direct the disposition of:

See item 10 on Cover Pages to this Schedule 13D.

(c) The persons identified in Item 2 of this Schedule 13D have not effected any transaction in shares of the Class A Common Stock during the preceding 60 days.

(d) Except as described in this Schedule 13D, no person has the power to direct the receipt of dividends on or the proceeds of sales of, the shares of the Class A Common Stock owned by the Reporting Persons.

(e) Not applicable.”

Item 7. Material to be Filed as Exhibits.

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Date: December 7, 2016

Attention. Intentional misstatements or omissions of fact constitute Federal criminal violations (see 18 U.S.C. 1001).

EXHIBIT 1

JOINT FILING AGREEMENT

In accordance with Rule 13d-1(k) under the Act, the undersigned hereby agree (i) to the joint filing on behalf of each of them of a statement on Schedule 13D (including amendments thereto) with respect to the Class A common stock, $0.01 par value per share, of Cumulus Media Inc. and (ii) that this Joint Filing Agreement be included as an exhibit to such joint filing, provided that, as contemplated by Section 13d-1(k)(1)(ii) of the Act, no person shall be responsible for the completeness and accuracy of the information concerning the other persons making the filing unless such person knows or has reason to believe such information is inaccurate.

In evidence thereof, the undersigned, being duly authorized, hereby execute this Agreement this December 7, 2016.

EXHIBIT 4

SUBJECT TO FRE 408 

CONFIDENTIAL

VOTING AGREEMENT

This Voting Agreement (this “Agreement”) is entered as of December 6, 2016, among CUMULUS MEDIA INC., a Delaware corporation (the “Company”); and CRESTVIEW RADIO INVESTORS, LLC (the “Stockholder”).

WHEREAS, concurrently with or following the execution of this Agreement, the Company is entering into that certain Refinancing Support Agreement dated as of December 6, 2016 (the “Refinancing Support Agreement”) with certain holders (the “ Supporting Noteholders”) of its 7.75% senior notes due 2019, pursuant to which the Supporting Noteholders have agreed, subject to the terms and conditions of the Refinancing Support Agreement, to tender their Notes in an exchange transaction for certain consideration, including 24.016 shares of the Company’s Class A Common Stock per $1,000 of Notes tendered in the Exchange Offer (the “Equity Consideration”);

WHEREAS, the Company will seek the approval of its stockholders for (a) the issuance of the Class A Common Stock comprising the Equity Consideration and (b) the amendment and restatement of its certificate of incorporation to increase the number of authorized shares of Class A common stock and effect the issuance of two new classes of common stock, Class D common stock and Class E common stock, at a meeting of its stockholders ((a) and (b), collectively, the “Transactions”);

WHEREAS, as a condition to its willingness to enter into the Refinancing Support Agreement, the Supporting Noteholders have required that Stockholder execute and deliver this Agreement; and

WHEREAS, in order to induce the Supporting Noteholders to enter into the Refinancing Support Agreement, Stockholder is willing to make certain representations, warranties, covenants and agreements with respect to the shares of common stock, par value $0.01 per share, of the Company (“Common Stock”) beneficially owned by Stockholder.

NOW, THEREFORE, in consideration of the premises and for other good and valuable consideration, the receipt, sufficiency and adequacy of which are hereby acknowledged, the parties hereto agree as follows:

For purposes of this Agreement, capitalized terms used and not defined herein shall have the respective meanings ascribed to them in the Refinancing Support Agreement.

Stockholder represents and warrants to the Company that:

(a)                (i) Stockholder owns beneficially (as such term is defined in Rule 13d-3 under the Securities Exchange Act of 1934, as amended, all of the Common Stock set forth on its signature page hereto, and (ii) except pursuant hereto and the agreements set forth on Schedule 1 hereto, there are no options, warrants or other rights, agreements, arrangements or commitments of any character to which Stockholder is a party relating to the pledge, disposition or voting of any of such Common Stock and there are no voting trusts or voting agreements with respect to the Common Stock.

(b)               Stockholder has power and authority to enter into, execute and deliver this Agreement and to perform fully Stockholder’s obligations hereunder. This Agreement has been duly and validly executed and delivered by Stockholder and constitutes the legal, valid and binding obligation of Stockholder, enforceable against Stockholder in accordance with its terms.

Stockholder hereby irrevocably covenants and agrees that at each annual, special or other meeting of the stockholders of the Company however called, or at any adjournment or postponement thereof, or in any other circumstances upon which a vote, consent or other approval of the Stockholders is sought, in each case, with respect to the Transactions, (i) when a meeting is held, it shall attend such meeting or otherwise cause such shares of Common Stock it holds to be counted as present thereat, and (ii) it will vote (or cause to be voted) all shares of Common Stock held by the Stockholder as of the date of such meeting that are eligible to vote on the matter or matters submitted to a vote of the Company’s stockholders at such meeting in accordance with the recommendation of the Board with respect to the Transactions.

Stockholder agrees that Stockholder will not, and will not permit any entity under Stockholder’s control to, deposit any of the Shares in a voting trust, grant any proxies with respect to the Shares or subject any of the Shares to any arrangement with respect to the voting of the Shares, in each case, in a manner that interferes with its obligations hereunder.

This Agreement shall terminate upon the earliest to occur of (i) the Consummation Date, (ii) the date on which the Refinancing Support Agreement is terminated in accordance with its terms and (iii) the date on which the Refinancing Support Agreement, or any of the Definitive Documents, is amended or modified, or any term thereof waived, without the prior written consent of the Stockholder.

Stockholder makes no agreement or understanding in this Agreement in respect of Stockholder’s representatives who serve as a director of the Company or any of its subsidiaries, and nothing in this Agreement: (a) will limit or affect any actions or omissions taken by such a director, including in exercising rights under the Refinancing Support Agreement, and no such actions or omissions shall be deemed a breach of this Agreement or (b) will be construed to prohibit, limit or restrict such a director from exercising fiduciary duties as a director to the Company or its stockholders.

It is understood and agreed by the parties hereto that money damages may be an insufficient remedy for any breach of this Agreement by any party, that such breach may represent irreparable harm, and that each non-breaching party shall be entitled to seek specific performance and injunctive or other equitable relief (without the posting of any bond and without proof of actual damages) as a remedy of any such breach, including an order of a court of competent jurisdiction requiring any party to comply promptly with any of its obligations hereunder. Notwithstanding anything to the contrary in this Agreement, in no event shall any party hereto or their representatives be liable to any other party hereunder for any punitive, incidental, consequential, special or indirect damages, including the loss of future revenue or income or opportunity, relating to the breach or alleged breach of this Agreement.

This Agreement constitutes the entire agreement of the parties hereto with respect to the subject matter of this Agreement, and supersedes all other prior negotiations, agreements, and understandings, whether written or oral, among the parties hereto with respect to the subject matter of this Agreement.

All notices, requests, claims, demands, and other communications hereunder shall be in writing and shall be deemed to have been given (a) when delivered by hand (with written confirmation of receipt), (b) when received by the addressee if sent by a nationally recognized overnight courier (receipt requested), (c) on the date sent by facsimile or e-mail of a PDF document (with confirmation of transmission) if sent during normal business hours of the recipient, and on the next Business Day if sent after normal business hours of the recipient, or (d) on the third day after the date mailed, by certified or registered mail, return receipt requested, postage prepaid. Such communications must be sent to the respective parties at the following addresses (or at such other address for a party as shall be specified in a notice given in accordance with this Section 9):

If to Stockholder, to the address or facsimile number that the Company has on record for the Stockholder.

(a)           This Agreement shall be governed by, and construed in accordance with, the laws of the State of New York, without regard to such state’s choice of law provisions which would require the application of the law of any other jurisdiction.

(b)           Each party hereto agrees that it shall bring any action or proceeding in respect of any claim arising out of or related to this Agreement in a New York state or federal court sitting in the Borough of Manhattan, New York, New York (the “Chosen Court”), and solely in connection with claims arising under this Agreement: (i) irrevocably submits to the exclusive jurisdiction and the authority of the Chosen Court; (ii) waives any objection to laying venue in any such action or proceeding in the Chosen Court; and (iii) waives any objection that the Chosen Court is an inconvenient forum, does not have jurisdiction over any party hereto, or lacks the constitutional authority to enter final orders in connection with such action or proceeding.

(c)           If any provision of this Agreement shall be held by a court of competent jurisdiction to be illegal, invalid, or unenforceable, the remaining provisions shall remain in full force and effect if the essential terms and conditions of this Agreement for each Party remain valid, binding, and enforceable.

(d)           This Agreement may be executed in one or more counterparts, each of which shall be deemed to be an original but all of which together shall constitute one and the same instrument.

(e)           All Section headings herein are for convenience of reference only and are not part of this Agreement, and no construction or reference shall be derived therefrom.

(f)            The obligations of Stockholder set forth in this Agreement shall not be effective or binding upon Stockholder until after such time as the Refinancing Support Agreement is executed and delivered by the Company and the Supporting Noteholders, and the parties hereto

agree that there is not and has not been any other agreement, arrangement or understanding between the parties hereto with respect to the matters set forth herein. If the Refinancing Support Agreement is not executed and delivered by the Company and the Supporting Noteholders within two (2) business days following the date hereof, then this Agreement will automatically be null and void ab initio.

(g) Neither party to this Agreement may assign any of its rights or obligations under this Agreement without the prior written consent of the other party hereto. Any assignment contrary to the provisions of this Section 12(g) shall be null and void.

IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed effective as of the date set forth in the first paragraph hereof.

Schedule 1