Singer: Lyle Lovett

Lyle Lovett has only had one single hit the top ten of the Country chart, “Cowboy Man” (1986). But he’s won four Grammy Awards, including Best Male Country Vocal Performance in 1989 for Lyle Lovett and His Large Band and Best Country Album in 1996 for Road to Ensenada. I think it’s safe to say he’s not that concerned about singles.

While Lovett has always been categorized as a country artist, even a brief encounter with his music reveals him to be influenced by jazz, gospel, and blues. When he performs with his Large Band, his sound is clearly more closely identified with blues than country.

As a songwriter, he pens lyrics both quirky and smart. Take this verse from “If I Had A Boat”:

Now the mystery masked man was smart, he got himself a Tonto
‘Cause Tonto did the dirty work for free
But Tonto, he was smarter, and one day said, Kemo Sabe
Well kiss my ass I bought a boat, I’m going out to sea

In addition to music, Lovett has acted in a number of TV shows and movies. He moved from the secluded world of underappreciated musician to the national stage in 1993 when he married Julia Roberts. They’d met on a movie set, were married after three weeks, and divorced in less than two years. America looked at Lovett, then looked at Roberts, and said, “Huh?”

Lovett’s Texas roots come through in both his phrasing and his attitude. He attended Texas A&M University, where he studied – get this – German and journalism. The most interesting fact about his time in college was his roommate, another eccentric musician — Robert Earl Keen. Imagine the jam sessions in that dorm room…