"How Do You Like Me Now?!" — Toby Keith

From How Do You Like Me Now?! (DreamWorks Records, November 2, 1999)
Written by Toby Keith and Chuck Cannon · Produced by James Stroud · Single released November 22, 1999

Sometimes a hit record does more than climb the chart. Sometimes it settles an argument. "How Do You Like Me Now?!" is the sound of a man who had been told his best song wasn't good enough, kept it anyway, bought it back with his own money, and then stood on a stage and sang it into the faces of the people who passed. The title is a taunt, and by the time the record was done the taunt had earned every exclamation point. It spent five weeks at No. 1, drove an album past three million copies, and won the ACM's Album of the Year. But the trophies aren't the story. The story is what Toby Keith was willing to risk before a single note of it ever reached the radio — and how little he had in the bank, careerwise, to risk it with.

WHERE HE STOOD

It's easy to read this as a star throwing his weight around. It wasn't. When Keith turned in the album that became How Do You Like Me Now?!, his momentum had gone cold. His 1997 record Dream Walkin' was the first of his career not to produce a single No. 1 — its singles stacked up at No. 2, No. 2, No. 5, and No. 40 — and he hadn't parked a single at No. 1 since "Me Too" in early 1997. By early 1999 one of his singles had missed the country Top 40 for the first time ever, a line no hitmaker wants to cross. He was not a man dictating terms from a position of strength. He was a proven artist watching his own heat drain away, convinced he was sitting on the song that would turn it back on, and unable to get the people paying him to hear it.

THE STANDOFF

Keith and his label, Mercury, had stopped hearing the same things in the same songs, and the gap kept widening until it swallowed a whole album. He turned in the new record; the label's verdict came back that most of it didn't work. And the track they pushed on hardest was the one he'd staked the whole thing on. "How Do You Like Me Now?!" had too much attitude, went the note. Might put listeners off. Wasn't what country radio was reaching for.

Keith had a different theory about what radio wanted — that nobody actually knows what radio wants until somebody plays it the thing it didn't know it was missing. So he made the move most artists never work up the nerve to make. He asked for his music back. Mercury told him he could have it if he paid for it, and he did: ninety-three thousand dollars of his own money to walk out owning the album his label had just handed back to him. No promise was stapled to that check. It was a bet, in cash, from a man on a downswing, that he was right and the building was wrong.

THE WALK ACROSS THE STREET

Then he made the bet pay before the songs ever did. Keith carried the album he'd just repurchased over to the brand-new Nashville arm of DreamWorks Records, run by the producer James Stroud, and sold it to them for two hundred thousand dollars — more than double what he'd spent to free it. In the space of an afternoon he had turned a rejection into a profit and a stalled career into a fresh one, on a startup label with something to prove of its own. Stroud produced the record and put it out on November 2, 1999, and the man who'd been told to start over now had a partner who heard the album the way he did.

Buying yourself out of a bad fit is one thing. Flipping it on the way to the label that would carry it to the top is another entirely. It was the first public glimpse of a truth about Keith that the next twenty years would make impossible to miss: he read the business of his own career as sharply as he read a hook.

THE WRONG FIRST PITCH

Even then the song had to survive one more near miss, and this one hit closer to home. DreamWorks didn't lead with it. They led with a ballad, "When Love Fades," and it stalled short of the Top 40 — a soft opening single going nowhere, the exact result that makes a new label second-guess the whole signing and makes an artist second-guess his second chance.

Keith didn't let it ride. He told them to pull it and put out the song he'd bought back and believed in from the beginning. They pulled "When Love Fades" and released "How Do You Like Me Now?!" on November 22, 1999. It was the make-or-break call of the entire project, and he made it himself, against the grain, twice over.

THE SONG ITSELF

He'd written it with Chuck Cannon, and by Keith's own account it nearly slipped through their hands. They'd just finished one song and rolled straight into the next, got a first verse down, and Keith was floored by it. Cannon shrugged — thought it was fine. That's the cruelty of a great fragment: a lone verse doesn't announce itself the way a finished song does, and the two of them let it sit for roughly six months before circling back. "I kept telling him this was gonna be a big song if we could just nail it," Keith remembered. When they finally sat back down, they nailed it.

What they nailed rides a nerve everybody's got. On its face it's a boy and the girl who never looked twice — the valedictorian, the one out of his league, remembered years down the road by the kid she couldn't be bothered with, now standing in front of her asking the only question that matters to him. The details are specific enough to sting: the crazy one, the boy who broke into the stadium and wrote her number on the fifty-yard line. But Keith always knew the song was bigger than one girl, and he said so plainly. "A lot of people become successful after they've been told they won't ever be," he explained. "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." He built a taunt with room in it for everyone. Every listener has a somebody they'd like to walk past on a good day.

And by the time he cut it, the song had turned autobiographical in a way no lyric sheet could capture. He'd been told no. He'd bought the no back and flipped it. He was, in the most literal sense the language allows, about to find out how they liked him now.

THE VIDEO

The clip Michael Salomon directed put the whole thing on screen without blinking. Keith plays the grown, successful version of the kid nobody picked, coming back to treat the girl who ignored him to a private midnight show on the hometown football field — the same fifty-yard line from the lyric, the boy's old grievance turned into a floodlit victory lap. It was vindication you could watch, aimed squarely at anybody the in-crowd ever waved off, and it welded the song's story to its singer's so tightly that most fans never thought to separate them.

WHAT HAPPENED NEXT

They liked him fine. Once radio finally had the song, it didn't just get played — it ran the place. "How Do You Like Me Now?!" hit No. 1 on Billboard's country chart and sat there five weeks, and by year's end Billboard ranked it the No. 1 country song of 2000. The album it anchored, the one Mercury had let go for pocket change, was certified platinum inside fifteen months and went on, by Forbes' accounting, to sell 3.1 million copies. At the 36th ACM Awards in May 2001 it won Album of the Year — handed to Keith as both the artist and, alongside Stroud, a producer of the record — and Keith was named Top Male Vocalist. Single and Song of the Year went elsewhere that night, to a waltz called "I Hope You Dance," which is the kind of loss no one apologizes for.

The sweetest part he saved for himself. Keith would talk about singing "How Do You Like Me Now?!" on an awards stage and letting his mind wander, mid-song, straight to the company that had told him to try again. He never had to name them from the podium. The song did it for him, into a live microphone, in front of the whole industry, night after night.

It also turned out to be a hinge. The record didn't just revive him; it opened the most commanding stretch of his career, the years when he became one of the defining voices of country radio and, not coincidentally, one of the shrewdest businessmen the format ever grew. All of it swings back to a single afternoon and a single refusal — a man on a cold streak who would rather be right and out ninety-three grand than wrong and comfortable.

WHY IT MATTERS

Plenty of hits prove an artist can sell. This one proved something narrower and harder to fake: that Toby Keith trusted his own ear over a building full of people whose job was to know better, at the exact moment his track record gave him the least standing to do it. He'd written a song, been told it was a liability, and answered by putting his own money behind his conviction — twice — and then staking the album on it a third time when the safe single died. Everything loud and unmistakable that came after started with that one refusal to take the note.

So if you've ever been told to stay in your lane, handed back your own work and told to try again, and found the grit to back yourself when the smart money said fold — this one's yours as much as it was ever his. He didn't just ask the question. He made the whole format stand there and answer it.

How do you like him now.

Toby Keith · "How Do You Like Me Now?!" · written by Toby Keith and Chuck Cannon · from How Do You Like Me Now?! (DreamWorks Records, 1999) · produced by James Stroud