The Beach Boys | Beastie Boys | Backstreet Boys | Pet Shop Boys | The Bowery Boys | BSC Young Boys | Boys & Girls Clubs of America | The Boys | Jersey Boys | Boys' Life | The Dead Boys | Lost Boys of Sudan | Boys' Brigade | The Lost Boys | the Beach Boys | Sport Boys | Newell's Old Boys | Geto Boys | Essex Boys | Bevin Boys | Bad Boys II | Trailer Park Boys | The Boys in the Band | Shirley Boys' High School | Momma's Boys | Henderson's Boys | Boys Town | Bad Boys Blue | Vienna Boys' Choir | The Rhythm Boys |
Wakefield is known for his collaborations with a number of important and well-known bands, including Red Allen, Don Reno, Jerry Garcia, David Grisman and the Greenbriar Boys.
After graduation he went to New York City where he eventually became one of the famous Greenbriar Boys, a popular folk group that was the main event at Greenwich Village's Gerde's Folk City, with Bob Dylan as his warm-up opening act.