Remember When Toby Keith Released ‘How Do You Like Me Now?!’

On this day in 1999, country music icon Toby Keith released his hit single, “How Do You Like Me Now?!”…


Madeleine O’Connell

| Posted on

November 22, 2022


8:26 am

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Toby Keith – How Do You Like Me Now

On this day in 1999, country music icon Toby Keith released his hit single, “How Do You Like Me Now?!”

This song served as the second single from his fifth studio album of the same name, which landed in the Top 10 and sold more than one million copies. “How Do You Like Me Now?!” was co-penned by Keith, now 61, alongside songwriter Chuck Cannon in response to those who showed they had no faith in his career and truly believed he would never make it in the music industry. 

“A lot of people become successful after they’ve been told they won’t ever be,” Keith said back in 2000 on his inspiration behind what would evolve into a signature track. “So people can relate to this. 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.”

After its release, the single became the fourth No. 1 hit of Keith’s career and spent five weeks at the top of the Billboard US Hot Country Songs chart. 

“How do you like me now? / How do you like me now? / Now that I’m on my way / Do you still think I’m crazy / Standing here today? / I couldn’t make you love me / But I always dreamed about livin’ in your radio / How do you like me now?” he sings in the chorus. 

YouTube video

In 2000, both the single and the album earned recognition at the Annual Academy of Country Music Awards ceremony. Keith was nominated for ACM Single of the Year and Song of the Year in addition to Album of the Year as both artist and producer.

The song ended up seeing great success, but it was no easy feat. Keith recalled the struggle it took to get his record label at the time, DreamWorks, to let him release “How Do You Like Me Now?!” as a single. 

He certainly made a statement to all those people that had no faith in him. In fact, Keith is still enjoying his massive career success as he continues to be honored for his career. 

On Tuesday, November 8, the “Should’ve Been A Cowboy” singer was recognized for his many achievements at the 70th Annual BMI Country Awards. He was honored by several artists during the star-studded event and even shared an acceptance speech on stage.

According to the press release, the BMI Icon Award is given to exceptional songwriters in recognition of their “unique and indelible influence on generations of music makers.” 

Previous recipients of the award include: Loretta Lynn, Willie Nelson, Merle Haggard, Dolly Parton, Kris Kristofferson, and Hank Williams, Jr., as well as multi-genre royalty Stevie Nicks, Little Richard, Patti Labelle, James Brown, and more. 

Toby Keith had remained out of the spotlight since revealing his cancer diagnosis with fans in early June, but he made his first public appearance when he popped up on stage at Jeff Ruby’s Steakhouse in Lexington, Kentucky on November 4.

The 2022 Breeders’ Cup took place on Friday (Nov. 4) and Saturday (Nov. 5) at Keeneland Race Course. After a day at the races, Keith enjoyed a night out with dinner at Jeff Ruby’s and shocked those in attendance when he took to the stage for his first performance in a year.   

He joined Ruby and the house band at the high-end steakhouse for an impromptu performance of his 2003 chart-topper, “I Love This Bar, Otis Redding’s “(Sittin’ On) The Dock of the Bay,” Lynyrd Skynard’s “Sweet Home Alabama,” and more. 

The country hitmaker and Songwriters Hall of Fame member took to social media over the summer to share his diagnosis with fans. 

“Last fall I was diagnosed with stomach cancer. I’ve spent the last 6 months receiving chemo, radiation and surgery. So far, so good. I need time to breathe, recover and relax,” the Nashville Songwriters Hall of Fame member wrote at the time. 

He added, “I am looking forward to spending this time with my family. But I will see the fans sooner than later. I can’t wait.”

After he announced his diagnosis, all of Keith’s upcoming concert appearances were canceled and no future dates have been announced.

Toby Keith recently revealed if he plans to return to the road in his first television interview in over a year. Click HERE for more.

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.