The Waylors

Background

Waylon was being managed by Buddy Holly's former first manager 'Hi-Pockets' Duncan who recommended Waylon to Buddy. With money out of his own pocket, Buddy produced Waylon's first record, a Rock & Roll version of 'Jolie Blon' & Waylon is considered to be Buddy's 'protoge'. In 1959 Buddy Holly hired Waylon Jennings to play electric bass for him during his "Winter Dance Party Tour". After a show in Clear Lake, Iowa, Holly chartered a plane for himself, Allsup and Jennings to avoid a long bus trip to Fargo, North Dakota. This is because the tour organizers provided very inadequate transportation & the buses broke down in freezing weather. Jennings gave up his seat to J. P. Richardson, who was suffering from a cold and complaining about how uncomfortable a long bus trip was for a man of his size. During the early morning hours of February 3, 1959, later known as The Day the Music Died, the charter crashed outside Clear Lake, killing all on board. Jennings and Allsup continued the tour for two more weeks, featuring Jennings as the lead singer. When the tour ended, he returned to his DJ spot on KLLL and performed regionally.

Phoenix and the Nashville sound

In 1961, Jennings lived briefly in Coolidge, Arizona working in radio, before moving to Phoenix, where he formed The Waylors, consisting in Jerry Gropp on the guitar and Richie Albright on the drums. Jennings and his band performed at a newly opened nightspot called JD's. The band earned a small fan base, eventually signing with the independent label Trend Records. In 1963, Jennings signed a contract with A&M Records. Jennings and The Waylors recorded an album on BAT called Waylon at JD's. Singer Bobby Bare, who covered Ian Tyson's "Four Strong Winds" and Jenning's "Just To Satisfy You", recommended Jennings to producer Chet Atkins, who signed Jennings to RCA Victor in 1965.

Jennings was accustomed to performing and recording with his own band, The Waylors; a practice that was not encouraged by powerful Nashville producers that instead used session musicians. Over time, however, Jennings felt limited by the Nashville sound's lack of artistic freedom. The music style publicized as "Countrypolitan" was characterized by orchestral arrangements, and the absence of traditional country music instruments. By 1972 he renegotiated his contract with RCA, that gave him complete creative control over his works. For the recording session, Jennings replaced the typical studio musicians of Nashville sessions with his band.

Later Years

By the 1980s the lineup included the additions of Ralph Mooney, Johnny Gimble, Rance Wasson, Gordon Payne, Jerry Bridges, Barney Robertson and Carter Robertson.

Mooney retired in 1996 and was replaced by Fred Newell, an established Nashville studio player. The band backed Jennings until 1999 when he formed a short-time project, The Waymore Blues Band, which was Jennings' "hand-picked dream team." Waymore Blues Band backed him until his death.

Now known as Waymore's Outlaws, the band continues today, with Tommy Townsend as lead guitar and vocalist. In 2014, the Outlaws came full circle by playing with Waylon's son and Richie Albright's namesake Waylon Albright "Shooter" Jennings for the first time on tour.