TOBY KEITH HAD ALREADY SCORED COUNTRY HITS WHEN HIS LABEL REFUSED TO RELEASE THE SONG HE BELIEVED COULD CHANGE HIS CAREER. HE LEFT — AND “HOW DO YOU LIKE ME NOW?!” BECAME THE BIGGEST COUNTRY HIT OF 2000. By the late 1990s, Toby Keith was successful but frustrated. His 1993 debut “Should’ve Been a Cowboy” had gone to No. 1, and more hits followed. But years of label changes involving Mercury, Polydor and A&M left Keith increasingly unhappy with how his music was being handled. One point of conflict was “How Do You Like Me Now?!,” a song Keith had written with Chuck Cannon. Keith believed in it. His label did not want to release it. When his relationship with Mercury ended, Keith regained rights to several songs and took the material elsewhere. DreamWorks Nashville signed him, and producer James Stroud—who had worked on Keith’s early records—returned to the studio with him. How Do You Like Me Now?! arrived in 1999. The title track was released as a single and did exactly what Keith had believed it could do. In 2000, it spent five weeks at No. 1 on Billboard’s country chart and finished as Billboard’s No. 1 country song of the year. More importantly, it began a different phase of his career. At DreamWorks, Keith followed with records including “You Shouldn’t Kiss Me Like This,” “I’m Just Talkin’ About Tonight,” “I Wanna Talk About Me” and “My List,” establishing the run that turned him from an established 1990s singer into one of country music’s dominant stars of the next decade. The song Mercury had declined to back did not simply survive the label change. It became the record that Keith carried through the door to the most commercially powerful stretch of his career.

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TOBY KEITH HAD ALREADY SCORED COUNTRY HITS WHEN HIS LABEL REFUSED TO RELEASE THE SONG HE BELIEVED COULD CHANGE HIS CAREER. HE LEFT — AND “HOW DO YOU LIKE ME NOW?!” BECAME THE BIGGEST COUNTRY HIT OF 2000.

Toby Keith was not an unknown singer begging for a first break.

By the late 1990s, he had already proved he could make country radio listen. “Should’ve Been a Cowboy” had gone to No. 1 in 1993, and more hits followed. He had the voice, the swagger, the Oklahoma confidence, and a growing audience.

But success did not mean control.

Years of label changes involving Mercury, Polydor, and A&M left Keith frustrated with how his music was being handled. He was winning enough to know he belonged, but not enough to feel the machine was fully behind him.

Then came the song he would not let go.

The Label Did Not Hear What He Heard

Keith had written “How Do You Like Me Now?!” with Chuck Cannon.

He believed in it.

His label did not.

That disagreement became more than a routine fight over a single. The song carried the exact energy Keith wanted to put forward — defiant, wounded, funny, arrogant, and built around the voice of a man who had been underestimated long enough to enjoy answering back.

It was not polite.

It was not soft.

It was Toby Keith looking straight at everyone who had doubted him and turning resentment into a hook.

Mercury did not want to release it.

Keith thought they were wrong.

Leaving Gave Him The Song Back

When his relationship with Mercury ended, Keith regained rights to several songs and took the material elsewhere.

That was the key turn.

The song did not stay buried inside a label disagreement. Keith carried it with him to DreamWorks Nashville, where he got a new shot and a familiar producer. James Stroud, who had worked on Keith’s early records, returned to the studio with him.

The timing was perfect.

Keith did not need to reinvent himself from nothing.

He needed the right company to understand what was already there.

In 1999, How Do You Like Me Now?! arrived.

This time, the title track got its chance.

The Song Answered For Him

Released as a single, “How Do You Like Me Now?!” did exactly what Keith had believed it could do.

In 2000, it spent five weeks at No. 1 on Billboard’s country chart and finished as Billboard’s No. 1 country song of the year.

That was not just a hit.

It was a public correction.

The label that had declined to back the song had watched Keith walk away with the very record that reopened his career on a bigger scale. The title itself made the success feel sharper, almost too perfect for the story.

“How do you like me now?”

Country radio answered by making it the biggest country song of the year.

DreamWorks Became The New Runway

The record did more than win one argument.

It began a new phase of Toby Keith’s career.

At DreamWorks, he followed with “You Shouldn’t Kiss Me Like This,” “I’m Just Talkin’ About Tonight,” “I Wanna Talk About Me,” and “My List.” The run turned him from an established 1990s hitmaker into one of country music’s dominant stars of the next decade.

That period sharpened his identity.

Keith became bigger, louder, more direct, and harder to separate from his own instincts. The songs could be romantic, comic, patriotic, rowdy, sentimental, or combative, but they carried a clearer stamp than before.

The fight over “How Do You Like Me Now?!” had proved something important.

Toby Keith knew what a Toby Keith record was supposed to feel like.

The Rejection Became Part Of The Fuel

Some career moments work because everything goes smoothly.

This one worked because it did not.

If Mercury had released the song when Keith first wanted it, it might still have been a hit. But the refusal, the split, the rights regained, and the move to DreamWorks gave the record an extra layer of meaning. It sounded like a comeback before he had fully disappeared.

It sounded like an artist taking ownership of his own temperature.

Not just asking radio for approval.

Demanding an answer.

That is why the song became a hinge in his career. It was not merely another single in a catalog. It was the moment his frustration turned into momentum.

What “How Do You Like Me Now?!” Really Leaves Behind

The deepest part of this story is not only that Toby Keith took “How Do You Like Me Now?!” to No. 1.

It is that he had to leave with the song before the song could become what he believed it was.

A 1993 breakthrough.

A string of hits.

Label changes.

Frustration.

A song written with Chuck Cannon.

Then Mercury saying no, DreamWorks saying yes, James Stroud back in the studio, and the biggest country hit of 2000 answering the whole argument in five words.

The record did not simply survive the label change.

It made the label change look like the beginning of Toby Keith’s real power.

He had already been successful.

But “How Do You Like Me Now?!” gave him something larger than success.

It gave him the sound of a man stepping out from under someone else’s decision and turning the rejection into the hook.

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Country Music

SAMMY KERSHAW HAD BEEN PLAYING COUNTRY MUSIC SINCE HE WAS 12. THEN DRUGS, ALCOHOL AND YEARS OF HONKY-TONKS WORE HIM DOWN SO BADLY THAT IN 1988, HE QUIT MUSIC AND WENT TO WORK REMODELING WALMART STORES. Sammy Kershaw grew up in Louisiana and started performing professionally as a boy. By his teens, his George Jones-influenced voice was already getting him opening slots for established country acts. But years of clubs, failed relationships, money trouble, drugs and heavy drinking pushed him in the opposite direction from Nashville. By 1988, Kershaw was done. He quit alcohol and drugs, walked away from music, and took a full-time job supervising remodeling work for Walmart stores. For roughly two years, the man who had spent most of his life onstage barely performed. Then songwriter Barry Jackson, who remembered hearing Kershaw years earlier in a Lafayette nightclub, tracked him down and urged him to make a demo. Kershaw gave music one more chance. The tape reached Mercury Records. After a showcase, Mercury signed him in 1990. Don’t Go Near the Water arrived in 1991. “Cadillac Style” reached No. 3 on Billboard’s country chart, “Anywhere but Here” also made the Top 10, and the album eventually went platinum. Two years later, “She Don’t Know She’s Beautiful” became Kershaw’s first No. 1. The comeback did not erase the years that nearly ended his career. It gave them a different consequence. The Louisiana singer who had once stepped away from every stage to rebuild his life eventually spent the 1990s carrying traditional honky-tonk back onto country radio — not as the young man who had first chased Nashville, but as someone who had already learned he could survive without it.

Country Music

KEITH WHITLEY AND EARL THOMAS CONLEY RECORDED “BROTHERLY LOVE” IN 1987. IT SAT UNRELEASED FOR FOUR YEARS. BY THE TIME IT BECAME A NO. 2 HIT, WHITLEY HAD BEEN DEAD FOR MORE THAN TWO YEARS. In 1987, Keith Whitley and Earl Thomas Conley were two of country music’s most recognizable voices. Conley was deep into the extraordinary run that would give him 18 No. 1 hits. Whitley was still climbing, only a year away from the breakthrough stretch that produced “Don’t Close Your Eyes,” “When You Say Nothing at All” and “I’m No Stranger to the Rain.” That year, they recorded “Brotherly Love,” written by Tim Nichols and Jimmy Alan Stewart. The song was built around two brothers who fight, compete and irritate each other, but remain bound by something stronger underneath. Then the recording disappeared into the vault. It was not released as a single. It did not appear on either man’s current album. On May 9, 1989, Whitley died from alcohol poisoning at 34. His career did not immediately stop with his death. RCA still had unreleased material, and records including “I Wonder Do You Think of Me” and “I’m Over You” became posthumous hits. Then, in 1991, someone went back to the duet with Conley. “Brotherly Love” appeared on Whitley’s posthumous Kentucky Bluebird and Conley’s Yours Truly. RCA released it as a single that August. Four years after the two men had stood in the studio together, their voices finally reached country radio side by side. The record climbed to No. 2 on Billboard’s country chart, spending 20 weeks on the chart. It later earned a Grammy nomination for Best Country Collaboration with Vocals. It also became the final Top 10 country hit for both singers. For Whitley, there could never be another session. For Conley, the result was different. He lived nearly three more decades, but country radio was changing, and none of his later singles returned him to the Top 10. So one recording from 1987 quietly became a dividing line neither man could have recognized when they made it. They walked into the studio with separate careers still moving forward. Country radio finally brought their voices together after one of those careers had already ended.

Country Music

EMMYLOU HARRIS WAS SEARCHING FOR SONGS AFTER GRAM PARSONS’ DEATH WHEN SOMEONE PLAYED HER A FIVE-SONG CASSETTE BY AN UNKNOWN TEXAS WRITER NAMED RODNEY CROWELL. ONE SONG WAS ENOUGH TO CHANGE BOTH THEIR LIVES. Rodney Crowell arrived in Nashville from Texas in 1972 with songs but no reputation. He fell into the circle around Guy Clark and Townes Van Zandt, learned the songwriter’s life, and landed an early publishing break through Jerry Reed. But he was still largely unknown when a cassette containing five of his songs reached Emmylou Harris. Harris was rebuilding after Gram Parsons’ death. While listening through demos for the album that became Pieces of the Sky, she heard Crowell’s “Bluebird Wine.” She stopped. Harris recorded it as the opening track of the album in 1975, then wanted to know who had written it. Crowell was tracked down. When Harris later passed through Austin, she offered him a plane ticket to Los Angeles. He took it and joined her newly formed Hot Band as guitarist and harmony singer, working beside players including James Burton and Glen D. Hardin. The job changed Crowell’s position in Nashville. Harris kept recording his songs. Then other artists followed. Waylon Jennings cut “Ain’t Living Long Like This.” The Oak Ridge Boys took “Leaving Louisiana in the Broad Daylight” to No. 1. Crystal Gayle had a No. 1 with “’Til I Gain Control Again.” Bob Seger turned “Shame on the Moon” into a major pop hit. For years, Rodney Crowell songs were more famous than Rodney Crowell. Then Diamonds & Dirt arrived in 1988. The album produced five consecutive No. 1 country singles: “It’s Such a Small World,” “I Couldn’t Leave You If I Tried,” “She’s Crazy for Leavin’,” “After All This Time,” and “Above and Beyond.” More than a decade after Harris first heard his cassette, Crowell had finally become the singer carrying his own songs to the top. The connection between them never disappeared. Nearly forty years after “Bluebird Wine,” Crowell and Harris recorded Old Yellow Moon together. In 2014, it won the Grammy for Best Americana Album. The young songwriter Emmylou Harris once hired for her band eventually stood beside her as an equal partner on an album bearing both their names.

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