WRKO serves as the Boston affiliate for ABC News Radio, Coast to Coast AM and This Morning, America's First News with Gordon Deal; syndicated personalities Joe Pags, John Batchelor and Bill Cunningham; the flagship station of The Howie Carr Show, and the home of radio personality Jeff Kuhner.

Besides its main analog transmission, WRKO simulcasts over the HD2 subchannel of sister station WZLX,[2] and streams online via iHeartRadio.

WLAW was acquired by General Teleradio in 1953 to serve as an upgraded facility for WNAC, replacing 1260 AM; it formally moved from Lawrence to Boston in 1957.

Following regulatory issues involving parent company Gencorp, in 1988 RKO General sold WRKO to Steve Dodge's Atlantic Ventures, which became American Radio Systems (ARS) in 1993.

[14][15] On June 17, 1953, General Teleradio changed WLAW's call letters to WNAC, moved the old 1260 AM format to 680 AM, and reassigned on- and off-air personnel.

WNAC remained a Mutual affiliate until the network, of which General Tire (by then doing business as RKO Teleradio Pictures) was a part-owner, was sold in July 1957.

WNAC, along with WRKO-FM and WNAC-TV (channel 7), were nearly sold by RKO General to NBC as part of a multi-city transaction and station trade between the two companies announced in March 1960.

[21][22] This arrangement wound up under review at both the FCC and the U.S. Department of Justice due to issues involving NBC's previous exchange of assets with Westinghouse Broadcasting in Cleveland and Philadelphia.

For the next decade, WRKO was one of Boston's top-rated radio stations, and absolutely dominant among its target audience of listeners in the 18-34 demographic.

Known to its listeners as "The Big 68", WRKO was home to such well-known personalities as longtime morning man Dale Dorman, Chuck Knapp, Joel Cash, Johnny Dark, J. J. Wright, J. J. Jeffrey, Harry Nelson (afternoon drive and later PD of WRKO in 1978), Shadoe Stevens, Frank Kingston Smith (who was known as "Bobby Mitchell"), Steve Anthony and many others.

In May 1975, WRKO's airborne traffic reporter, "The Red Baron" (Rick Blumberg), joined the morning team with Dale Dorman and Bill Rossi.

The station tried to compete with the surge in FM listening, first with a short-lived focus on album cuts and later by switching to more of an adult contemporary music format, featuring a morning program with market legend Norm Nathan.

On September 27, 1981, the station switched to an all-talk format; at 6:00 p.m. on that date, Justin Clark played the last song, "American Pie" by Don McLean.

[43] As part of the settlements worked out in Boston, New York, Memphis, Chicago, Fort Lauderdale, Los Angeles and San Francisco, WRKO and its FM sister station, WROR (the former WNAC-FM and WRKO-FM; now WBZ-FM), were sold to Atlantic Ventures Corp., operated by cable television executive Steve Dodge, for $28 million in November 1988;[44] Gencorp only received $17.5 million, with the rest being awarded to past applicants that had competed for the licenses.

[44] As the combined company would have controlled 59 percent of advertising revenues in the Boston market, as well as three of the top five radio stations, in April 1998 the Department of Justice ordered CBS to divest WRKO, WEEI, WAAF (now WKVB), and WEGQ (now WEEI-FM), as well as KSD and KLOU in St. Louis and WOCT in Baltimore, as a condition of its approval of the merger.

The station itself made news in early November 2006, when late morning host John DePetro was fired following his on-air description of gubernatorial candidate Grace Ross as a "fat lesbian".

Finneran was dropped from the lineup at the end of May 2012;[63][64] his replacement, Michele McPhee, was paired with Fineburg until October 31, when Jeff Kuhner was moved into the time slot.

[65][66] Massachusetts state trooper Grant Moulison was WRKO's lead traffic reporter from 1985 until retiring from the force in April 2006, with 32 years of service behind him.

[69][70] WRKO dropped Rush Limbaugh again in May 2015, citing the expenses for running Limbaugh had risen too steeply;[71] Kuhner was moved to the midday time slot; the replacement morning show, co-hosted by Kim Carrigan and Doug "VB" Goudie, featured material from Boston.com as part of a content partnership with The Boston Globe.

[74] iHeartMedia acquired WRKO, WBZ, WZLX and WKAF as part of a multi-market station and asset swap between it and Entercom; to meet ownership limits set by the FCC, WKOX was designated to be divested.

[81] In late November 2018, WRKO moved Jeff Kuhner back to morning drive and Doug Goudie to middays, with Kim Carrigan exiting the station.

[82] Two years later, iHeart laid off Goudie,[83] and announced a new show to be hosted by Grace Curley and produced by the Howie Carr Radio Network, which was launched on January 4, 2021.