One of the most legendary stations in Boston radio history has been WBCN (104.1), which has shifted between rock and alternative music since the late sixties. The station's Program Director in the late seventies was Oedipus, who the Police have credited for launching their success in the United States by being the first to play "Roxanne." Oedipus remained with the station until the early 2000s.

In the nineties it was one of the top-rated alternative stations in America. Competitor WFNX (101.7) has not been a ratings leader, but has also gained national acclaim as an alternative station. Boston has also been the home of one of America's most legendary top 40 stations of the sixties, WRKO.

In 1921 the first AM stations that could be heard in Boston, included Westinghouse's WBZ, licensed to Springfield on 833 AM, American Radio and Research's 1XE licensed to Medford Hillside on 855 AM and Irving Vermilya's 1ZE on 1200 AM. WBZ became the market's first 50,000 watt station in the thirties. National networks rose in the twenties and thirties. WBZ carried NBC Blue programming while WNAC (1230) aired NBC Red as well as Yankee and Mutual programming. WNAC was owned by the Yankee Network, headed by John Shephard. Yankee's shows could also be heard on WNBH (1310) and WLLH (1370). CBS shows aired on WEEI (590) and WORC (1280).

WNAC was one of the three earliest licensees in the market. It was the flagship station of the Yankee Network. In 1941 WNAC moved from 1230 to 1260 on the AM dial, following broad sweeping changes that affected the radio industry nationally, set by the FCC, in which several stations were assigned new dial positions. WNAC came under the ownership of General Tire, which later merged with RKO to become RKO General. In 1953, General Tire bought WLAW (680), licensed to Lawrence, and its sister 93.7 FM from Hidreth and Rogers. Due to ownership limitations ruled by the FCC, General Tire was required to sell the 1260 frequency. WNAC then moved to 680 AM.

In 1960 the FM became WRKO. Six years later it broke away from the WNAC AM simulcast and became an automated rock station called "Arko-matic." As the Yankee Network ended in 1967, WNAC AM became WRKO AM and began playing top 40. It became one of the market's top stations for the next decade. After hit music faded from the AM dial in the early eighties, the format shifted to talk. With the folding of RKO General over an accounting scandal, ownership changed to Atlantic Ventures and eventually Entercom.

Another radio ownership controversy ended in 1972 when the towering influence of the Boston Herald-Traveler in the market was challenged and the owner was forced to divest its properties. Rival licensees took the case all the way to the Supreme Court to break up its ownership of WHDH, which was a combination of 850 AM, 94.5 FM and TV channel 7. The Herald-Traveler then went out of business, although its newspaper division was sold to competitor the Record-American, which later became the Herald-American.

As rock and roll music began to spread around the country in the fifties, Boston's outlet for the raging new style was WILD (1090). It had launched as classical station WBMS in 1946. Under the ownership of the Friendly Group the station went pop in 1950. The call letters became WILD after the station was purchased in 1957 by Bartell, who had ushered in rock and roll in other major markets. Bartell sold in 1966 to Leonard Walk, who sold to Sheridan in 1973. WILD then switched format to urban music. It was picked up in 1980 by African American businessman Kendall Nash, who held the station until his death in the late nineties. His widow Bernadine Nash sold the station in the early 2000s to Radio One for $5 million.

WMEX (1510) was Boston's hot top 40 station in the sixties prior to WRKO entering the competition. But WRKO took the market crown for hit music as the RKO chain's affiliation with consultants Bill Drake and Gene Chenault created a national trend with high energy, tightly programmed top 40 stations. In 1975 WMEX flipped to talk and then three years later the call letters changed to WITS. Its main competitor was CBS station WEEI (590). In the early eighties the format briefly flipped to big bands as "Memories" before going dark. The station came back on the air later in the decade as WSSH, first under Noble Broadcasting, and then went through a series of format changes.

Disco music became huge in the late seventies, and with the rise of disco came the rise of WNTN (1550). It had originally gone on the air in 1968 as an adult hits station. As the station was gaining notoriety as a disco station, the format was picked up on FM by Kiss 108. Since FM had better sound quality, music listeners in general migrated to FM with the fine-tuning of technology, allowing FM signals to finally be heard in moving vehicles without reception issues.

Kiss 108 picked up its WXKS call letters and disco format in 1979 after beautiful music combo WWEL AM/FM changed hands from Sherwood Tarlow to Hawaii Congressman Cecil Heftel. Both the AM and FM had been in the market's ratings cellar for years with the beautiful music format, which could also be heard in the seventies on WHET (1330), owned by Ted Jones. Heftel hired talented programming talent, changed the call letters, changed 1430 AM to the "Music of Your Life" nostalgia format, and delivered the disco hits on 107.9 FM. Kiss 108 quickly shot to the top of the ratings and became a top station in the market throughout the eighties, even after the burning out of disco, as Kiss 108 transformed into a contemporary hits station and ownership changed to Pyramid.

Top 40 stations continued to rule the market by the end of the eighties. WXKS continued to be number one in the market with strong competition from Ardman's WZOU (94.5). WRKO placed regularly as a top three station delivering news on 680 AM. As in many major markets, the beautiful music format did well for WJIB (96.9), owned by Emmis. Infinity's WBCN had built a heritage by the end of the decade as the market's rock leader. A series of challengers failed to come close to posting the ratings generated by WBCN.

Several AM stations still did well in the eighties besides WRKO, such as New England TV's talk station WHDH (850), Helen's news station WEEI (590), Plymouth Rock's WPLM (1390) simulcast of 99.1's big band programming, Pyramid's big band competitor WXKS (1430) and Nash's urban contemporary station WILD (1090).

Throughout the nineties, Boston's top radio stations continued to be WBZ, WJMN, WXKS-FM, WBCN and WRKO-AM. Following the Telecom Act of 1996, which loosened ownership limits, several big companies began to take over significant percentages of major market radio stations. Boston was one of the first markets to experience the wave of corporate consolidate that would sweep the nation.

In 1997 CBS Radio owned WBZ-AM, WBCN, oldies station WODS (103.3) and classic rocker WZLX (100.7). Chancellor Media owned WJMN and WXKS AM/FM. Greater Media owned adult contemporary WMJX (106.7), country WKLB (96.9 then moved to 99.5), oldies WROR (105.7), adult alternative WBOS (92.9) and Smooth Jazz WOAZ (99.5 then moved to 96.9). American Radio Systems, which had grown out of Atlantic Ventures, owned several stations as well: WRKO-AM, hot ac WBMX (98.5), sports leader WEEI (850), rocker WAAF (107.3) and oldies WEGQ (93.7). The last independent to remain competitive in the market was Charles River, whose WCRB (102.5) was one of the highest rated major classical stations in the country at that time.