Lyle Lovett

An heir to such eccentric literary Texas troubadours as Guy Clark, Walter Hyatt, and Townes Van Zandt, Lyle Lovett laid the groundwork for the alternative country and Americana movements with his eponymous 1986 debut and its 1987 successor, Pontiac. Filled with incisive character studies, lyrical ballads, and dry wit, the two albums established Lovett as a distinctive singer/songwriter whose appeal extended far outside of country.

Already rooted in the dusty eclecticism of Texas country, a subgenre where folk intertwined with Western swing, Lovett expanded his musical reach with Lyle Lovett & His Large Band, a 1989 album where he showcased a supporting band well-versed in swing and jump blues. He reached the apex of his popularity in the early '90s with the albums Joshua Judges Ruth and I Love Everybody crossing over to an adult-oriented pop audience, while 1996's The Road to Ensenada won the Grammy for Best Country Album. Lovett's songwriting and recording slowed in the 21st century -- he took an extended ten-year hiatus between Release Me in 2012 and 12th of June in 2022 -- but maintained on outsized presence on the Americana and Texas country scenes, thanks to regular performances with his Large Band.