Gill began his career in the 1970s in Bluegrass bands before joining the country rock band Pure Prairie League in 1979 as a singer and guitarist. The Gill-sung "Let Me Love You Tonight" became the band's biggest hit, reaching #1 on the Billboard Adult Contemporary chart and #10 on the Hot 100 in 1980. The next year he left to join Rodney Crowell's backing band, The Cherry Bombs, then signed as a solo act with RCA Records in 1983, putting out three modestly successful albums: Turn Me Loose, The Things That Matter, and The Way Back Home. After transferring to MCA in 1989, Gill's career kicked into motion: his first MCA disc produced the #2 hit "When I Call Your Name", with his next four albums each producing several Top 10 hits (including four number 1 hits from I Still Believe in You). It was at MCA that Gill developed his signature style, blending mainstream country and bluegrass, often with a high emphasis on ballads.
Although Gill's fortunes faded in the late 1990s, he continues to record to this day. He can frequently be heard singing backing vocals on just about everything.
Tropes present in Gill's work:
- Advertised Extra: On Chris Young's "Sober Saturday Night", to which he contributes a barely-noticeable backing vocal and a brief guitar solo.
- Distinct Double Album: These Days is a 4-disc set on which each disc has a distinctly different style.
- Early Installment Weirdness:
- He happened to join Pure Prairie League just as they were shifting their sound from country rock to soft rock; they even added a saxophone player to their lineup. "Let Me Love You Tonight", while still a frequently-heard oldie, has Gill sounding really out-of-place, if you're familiar with his later country hits.
- His 1980s work for RCA is noticeably more pop, with a high emphasis on keyboards instead of the neotraditionalist feel he built on MCA.
- Record Producer: For most of the 90s and into the 2000s, he was produced by Tony Brown, a former session keyboardist also known for producing Reba McEntire and George Strait.
- Signature Style: Softly produced country with his trademark high, smooth tenor voice. Some of his songs also feature the fluid, high-toned "crying steel" playing of pedal steel guitarist John Hughey, such as "Look at Us".
- Something Completely Different: In 2005, he and Rodney Crowell did an album with Crowell's former backing band, The Cherry Bombs. The project and album were titled The Notorious Cherry Bombs.
- Truck Driver's Gear Change: "Oklahoma Swing", a duet with Reba, starts off in B-flat with Vince, then drops down to E-flat for Reba. It then stays in the lower key, except for an instrumental break that returns to B-flat.
- Vocal Evolution: His voice had a somewhat stuffy sound when he was in Pure Prairie League, but became smoother in his solo work. It also started to become more weathered in the 21st century.
- Your Cheating Heart: "Which Bridge to Cross (Which Bridge to Burn)" has a man conflicted over two lovers.