Outlaws, by definition, operate outside the system. By that criteria, there was no greater outlaw in country music during the '70s than Tompall Glaser, a running partner of Waylon Jennings and Willie Nelson who never quite managed to play the game and become a star, or even have that many hits despite being showcased on the era-defining 1976 compilation Wanted! The Outlaws, and despite chasing after outlaw cash whenever the opportunity arrived. Such contradictions were inherent within Tompall Glaser, whose attitude was quintessentially outlaw -- tales of feuds and fallouts ran rife in his career -- but he would try to bend his music to fit the times, all in hopes of scoring that one elusive hit single. Hits are only one yardstick of impact and it's undeniable that Tompall was a major player, both as a member of the Glaser Brothers and as a solo act in the '60s and '70s, providing a musical template -- and with his Hillbilly Central studio, a place for outlaws to record just outside of the mainstream of Nashville, an opportunity Waylon seized for the game-changing Honky Tonk Heroes -- and the ornery temperament that forever became known as outlaw country.

Before he struck out on his own, Tompall was the oldest member and lead singer of the Glaser Brothers, a family trio from Spaulding, Nebraska. As a child, Glaser taught his younger brothers Chuck and Jim how to sing harmony to his lead, laying the seeds for their professional debut in the late '50s as Tompall the Glaser Brothers. While Tompall was in the military in 1956 and 1957, Jim and Chuck had a radio show in Hastings, Nebraska and their father Louis helped his boys score spots in local shows. All this work began to pay some dividends in the back half of 1957, beginning with an appearance on Arthur Godfrey's radio show, a performance that earned the attention of Marty Robbins. The singer signed the brothers to his label, Robbins Records, releasing the single "Five Penny Nickel" to little attention and then selling their contract to Decca Records in 1959. By that time, the brothers had relocated to Nashville, but Music City couldn't quite figure out a way to market the sibling singers, attempting to fashion them as a folk group to little success. In the meantime, the Glaser Brothers picked up a lot of studio work as backing singers, most notably appearing as support for Marty Robbins; Jim was one of the harmony vocals on Marty's big hit "El Paso."

The next big phase in the Glaser Brothers' career arrived after Chuck returned from a stint in the Army from 1959-1961, when Johnny Cash hired the group as a supporting touring act. This connection led to the attention of Jack Clement, a songwriter and producer who often worked with Johnny. Clement brought the Glaser Brothers to MGM Records, which signed the group in 1966. By the end of the year, the group cut "Streets of Baltimore," a Tompall original co-written with Harlan Howard that turned into a standard, but not a hit for the Glasers; instead, Bobby Bare took it up the charts within the year. The Glaser Brothers continued to record steadily with Clement, often cutting songs written by the producer, songs with cinematic scope and an intriguing blend of folk storytelling, country melodies, and pop productions. As distinctive as these singles were, the Glaser Brothers had a rough time reaching the upper portions of the country charts; "California Girl (And the Tennessee Square)" managed to get to number 11, but most of their singles of the late '60s -- including "Gone, on the Other Hand," "Through the Eyes of Love," "The Moods of Mary," and "One of These Days" -- stalled in the middle of the charts. Even if they weren't turning into stars, the Glaser Brothers were working their way into the business of Nashville, opening up a publishing company -- spurred on by Chuck's discovery of singer/songwriter John Hartford, best known for "Gentle on My Mind" (the Glasers cut the song early in 1967) -- and starting a studio, while Jim started to gain attention as a songwriter, co-authoring Gary Puckett's number four hit from 1968, "Woman, Woman."

The Glaser Brothers had their first Top Ten hit in 1971 with "Rings," a cover of a light AM pop hit by Cymarron, a somewhat ironic situation because instead of getting poppier, the group was getting a little looser, with Tompall sketching out the blueprint for his outlaw country sound on the singles "Faded Love," "Sweet, Love Me Good Woman," and "A Girl Like You." As the music was shifting, so were relationships between the brothers, leading to a familial fallout in 1973. The brothers went their separate ways, with Chuck opting to operate a booking agency while Jim and Tompall pursued their own careers. Jim never managed to gain much traction but Tompall carved out a niche as a cult artist, shaping the sound of country music in the '70s as a performer and through his studio, Hillbilly Central, which he inherited in the split. Tompall and friends, including Waylon Jennings and Billy Joe Shaver, recorded albums there, creating the earthy, lived-in sound of outlaw country. Although it was credited to the Glaser Brothers, Glaser's first solo album was 1973's Charlie, and it and its singles, including its title track, were modest hits, but its 1974 follow-up, Tompall Glaser Sings the Songs of Shel Silverstein, gave Tompall some momentum thanks to the single "Put Another Log on the Fire (Male Chauvinist National Anthem)," a cheerfully offensive tune that peaked at 21, making it Glaser's biggest hit.

This, along with his prominent position on the 1976 compilation Wanted! The Outlaws -- Waylon Jennings pushed for his inclusion on what would be the first country album to sell a million copies -- seemed to set Tompall Glaser up for stardom, but it didn't quite turn out that way. He delivered one more album for MGM, 1975's The Great Tompall and His Outlaw Band, before leaving for ABC, where he delivered the confusingly titled Tompall Glaser and His Outlaw Band in 1977, following it later that year with Wonder of It All. These two records sounded slicker than any of his MGM work, yet that didn't help him gain a larger audience. Soon enough, Tompall blew whatever money he had from Wanted!, fell out with Waylon, and patched up his relationship with his siblings, and the Glaser Brothers signed with Elektra's new Nashville branch in 1978.

Three years later, the Glaser Brothers released their comeback Lovin' Her Was Easier (Than Anything I'll Ever Do Again), which unexpectedly gave them their biggest hit ever in the form of its title track, which went all the way to number two on the charts. Its commercial success signaled that the album had a more commercial sound; Lovin' and its 1982 sequel After All These Years were the opposite of Tompall's unkempt outlaw years and, for the first time, the group's commercial gambit paid off. After this success, the group split again, with Jim going off to a solo career. Chuck and Tompall briefly replaced him with Shaun Nielsen, a veteran of Elvis Presley's supporting group the Imperials, but soon the Glaser split for good. Tompall released one last solo album in 1986 -- the slick Nights on the Borderline, containing revivals of both "Streets of Baltimore" and "Put Another Log on the Fire" -- before selling Hillbilly Central and retreating from the spotlight. He died in Nashville in August of 2013. ~ Stephen Thomas Erlewine, Rovi