HomeEntertainmentMusicCountry Throwback: Toby Keith Releases ‘How Do You Like Me Now?’ 21 Years Ago Today

Country Throwback: Toby Keith Releases ‘How Do You Like Me Now?’ 21 Years Ago Today

by Matthew Wilson
Photo credit: Kevin Winter/ACMA2014/Getty Images for ACM

Toby Keith’s song “How Do You Like Me Now?” can legally drink today. It’s been 21 years since the country musician released the hit single.

The tune released in November 1999 as the title track for Keith’s album of the same name. Upon release, the song proved instantly popular and spent five weeks at the top of the charts. Keith co-wrote the song with James Shroud based upon his own experiences in the industry.

The original title for the song was “You Never Loved Me Before, So How Do You Like Me Now?” According to Country Music Notes, Keith introduced the song to Shroud during a writing session. The title was inspired by one of Keith’s catchphrases. Together, the two created a universal and relatable song of overcoming perseverance.

“A lot of people became successful after they’ve been told they won’t ever be, so people can relate to this,” Keith said. “It can be about an old flame or a boss or a teacher – whatever it means to each individual. It was a fun song to write.”

Toby Keith’s Personal Experiences Inspired the Song

The song is based upon Keith’s experiences of trying to break into the country music industry. According to The Boot, he had meetings with record executives who turned down his music. A discouraged Keith wanted to give up on his dream.

“I had a meeting with Jimmy Bowen at Capitol. When I went in there and played, it was on a cassette, and he was just hitting fast forward. He’d play a verse and a chorus, and he’d hit fast forward,” Keith said. “We got done, and he goes, ‘Well, that’s all good and fine. You sing good, but you need to go back to the woodshed and work on your songwriting. These songs aren’t going to cut it.’”

Finally, a friend introduced Keith to Harold Shedd, producer and the head of a record label. Shedd liked Keith’s performance and songs and signed him to Mercury Records. But Keith faced another challenge when the label tried to change his image. They wouldn’t let Keith write the songs that he wanted to.

“So then, I started saying, ‘These are the songs that I want to cut that you guys will never record,'” Keith said. “I changed producers, and I went with James Stroud, and he just said, ‘You bring ‘em, I’ll cut ‘em.’ And so, we cut everything I wanted to record.”