5 Hall of Fame Worthy Songs from Toby Keith

Toby Keith died in February after a long battle with stomach cancer and a longer career in country music. The former football player and oil rig worker kicked the doors off of the country music world when he released his chart-topping debut single in the early ‘90s  He went on to release a stack of albums and take 20 singles to No. 1 on the Billboard charts.

Today, the Country Music Association announced the Country Music Hall of Fame class of 2024. Keith, John Anderson, and James Burton will join the hallowed institution at the medallion ceremony later this year. For now, let’s take a look back at five of the songs that made Keith a shoo-in for the Hall of Fame.

“Should’ve Been a Cowboy”: Toby Keith’s Debut Single

“Should’ve Been a Cowboy” introduced Keith to the world as both a performer and songwriter. He released it in February of 1993 as the lead single from his self-titled debut album. It topped the Billboard Hot Country Songs chart and landed at No. 98 on the publication’s all-genre Hot 100 chart. It went on to be the Oklahoma native’s signature song.

After Keith passed many artists worked the song into their setlists as a tribute. However, no cover will ever be as good as the original.

“Who’s That Man”

Keith penned “Who’s That Man” and released it as the lead single from his 1994 sophomore album Boomtown. It went on to be his second chart-topping single. This one may not be as well-remembered as his debut single, but it still stands as a testament to his strength as a songwriter and storyteller.

“How Do You Like Me Now?!” Toby Keith’s Final Single of the ‘90s

Keith co-penned “How Do You Like Me Now?!” with Chuck Cannon. It was the second single and title track from his 1999 album. It was the final single and final No.1 of the ‘90s, a decade in which he ruled the airwaves.

After recording the entirety of the album, executives at Mercury rejected all but two songs. As a result, he terminated his contract and moved to Dreamworks Records. This was the first of two chart-toppers from the album.

“As Good as I Once Was”

Keith co-penned this song with Scotty Emerick and released it as the second single from his ninth studio album Honkytonk University in 2005. It’s a tongue-in-cheek song about a middle-aged guy looking back on his glory days. It was also Keith’s way of showing the world that he still had it more than a decade into his career.

“Weed with Willie”

Keith co-penned this one with Emerick and included it on his 2003 album Shock’n Y’all. The record went to the top of the Billboard Country Albums chart. Additionally, it produced two chart-topping singles—“American Soldier” and “Whiskey Girl.” However, neither of those hits is as fun as this song about taking one too many hits with country icon and legendary stoner Willie Nelson.

Maybe the best part about this song is that it’s based on true events. According to Songfacts, Keith and Emerick met Nelson for the first time when they visited him on his tour bus to ask him to sing on “Beer for My Horses.” Nelson agreed to be on the song which would later become a No. 1 hit. He also got both Emerick and Keith baked like apple pies.

This is the most fun you’ll ever have listening to Toby Keith and that’s a high bar.

Featured Image by Rick Diamond/Getty Images for Shock Ink