MERCURY SAID THE ALBUM HAD NO HIT ON IT. TOBY KEITH BOUGHT IT BACK — AND ONE SONG OFF IT SAT AT NO. 1 FOR FIVE WEEKS. Near the end of his Mercury deal, Toby was told the record he’d made didn’t have the hit they wanted. He talked his way out, paid to own the songs, and took them to DreamWorks. Even there, nobody wanted “How Do You Like Me Now?!” as the first single. Radio had gone female-driven, they argued; a man couldn’t sing that line to a woman. So the ballad “When Love Fades” went out instead, and it never cracked the Top 40. Toby quit waiting on them and picked up the phone himself, working down a list of about 30 radio programmers. Whatever he said on those calls, the label’s plan didn’t survive the week. The song went to No. 1 and stayed five weeks. Billboard named it the top country song of 2000. So what does a man say to 30 strangers that his own label wouldn’t say for him?

Toby Keith, the Label That Said No, and the Song That Wouldn’t Quit

At the end of Toby Keith’s Mercury run, the message was blunt: the album he had cut did not have the hit the label wanted. Mercury even pulled two songs from the project for Greatest Hits Volume One and told Toby Keith to keep moving. Toby Keith did not exactly move on quietly. He pushed for his release, bought back the songs, and carried the project over to DreamWorks, where How Do You Like Me Now?! would become one of the defining country releases of 1999. The album was issued on November 2, 1999, and produced by James Stroud.

Even then, the story did not begin with victory. DreamWorks was wary of the title track and chose “When Love Fades” as the first single instead. That choice did not land the way the label hoped. Keith later recalled that the song stalled while the real fire was sitting on the shelf. In interviews, he said he went directly to radio programmers himself and told roughly 30 of them to play “How Do You Like Me Now?!” instead. According to Keith’s account, that changed everything fast.

The confidence behind that move came from rejection. Keith has said he got hard looks when he submitted the song, and that people inside the company kept asking about the female audience. But the song’s whole point was its nerve: a proud, direct answer to being overlooked. Once Keith believed in it, he stopped waiting for permission. He later summed up that turning point by saying that after he took the album “across the street,” it became hard to tell himself no.

The result was bigger than anyone at Mercury or DreamWorks had expected. “How Do You Like Me Now?!” reached No. 1 on the country chart and stayed there for five weeks. It also crossed to No. 31 on the Hot 100, giving Toby Keith his first pop Top 40 hit. Billboard later named it the top country song of 2000, and the album earned a Platinum certification and an ACM Album of the Year award. The title track was written by Toby Keith and Chuck Cannon.

That is the part that still lingers: not just the hit, but the way it arrived. Toby Keith did not wait for the industry to agree with him. He called the stations, backed his own instinct, and let the song do the arguing.

One call at a time, Toby Keith turned doubt into a No. 1 record.

HIS DAD LOST HIS RIGHT EYE IN THE ARMY AND NEVER COMPLAINED. SIX MONTHS BEFORE 9/11, A HIGHWAY CRASH KILLED HIM — AND THAT’S WHERE THIS WEEK’S NO. 11 SONG BEGINS. H.R. “Hoss” Covel lost his right eye serving in the Army and came home without griping about it once. In March 2001 a highway crash killed him. Six months later his son watched the towers fall and wrote a song in roughly 20 minutes — for his dad. Then Toby Keith refused to record it. For months “Courtesy of the Red, White and Blue” lived only on USO stages, and the reason he wouldn’t put it on tape had nothing to do with his label. This week, after America’s 250th birthday weekend, it re-entered the Billboard Hot 100 at No. 11: 15.3 million U.S. streams, 2.6 million in airplay audience, 6,000 downloads, No. 2 on both Streaming Songs and Digital Song Sales. In 2002 it stalled at No. 25. “Red Solo Cup” got him to No. 15.

FORGET THE ARENAS. RILEY GREEN’S FAVORITE SEAT IS ON A BULLDOZER. Riley told Theo Von on This Past Weekend that the 1,780 acres he owns in Alabama, roughly two Central Parks, never came as one big purchase. It started with 141 acres belonging to uncle Bill, his granddaddy Buford’s brother, the ground Riley grew up running around on. He bought that piece first. Every trip home since, he’s been on the phone with the neighbors asking if anybody’s selling. Now all of it touches. He doesn’t hire the work out, either. He clears the fields, cuts the dirt roads and digs the ponds on his own equipment. Out on tour he’s already deciding which field is waiting for him when the bus pulls in. And here’s what it actually gives him. Not investment, not acreage, not something to brag about on a podcast. Riley said the seat of that machine is “one of the only places I forget about my phone.” The No. 1s are nice, he admitted, but they aren’t the thing that satisfies him. A country star with a sold-out tour, and the happiest he gets is alone on a bulldozer in Alabama, covered in dirt, nobody able to reach him.

IT TOOK CHRIS STAPLETON TEN MINUTES TO WRITE THE SONG. IT TOOK NEARLY A DECADE BEFORE HE’D RECORD IT. Sometime in the mid-2000s he was at his girlfriend’s apartment, waiting on her to get ready. Morgane wasn’t his wife yet. She told him that if he was going to hover, he might as well write a song. Ten minutes later he had “Daddy Doesn’t Pray Anymore.” His father was alive, and would be for years yet. Herbert Stapleton worked the Kentucky coal mines, a straight arrow who had said grace at every meal his son had ever eaten with him. So where does a man get the idea to write that title about a father like that? It came from one evening at his parents’ table in Staffordsville, over something that happened exactly once and never happened again. Herbert died at home in October 2013, at 67. Chris has said the song “got weight after my father passed away,” and only then did he cut it, for Traveller. At an industry event in Nashville in early 2015 he set a chunk of coal on a stool beside him — the first piece his father ever mined — and dedicated the next song to him. The title was true by then. It wasn’t true the night he wrote it, and he was still telling the story of that dinner ten years on.

MERCURY SAID THE ALBUM HAD NO HIT ON IT. TOBY KEITH BOUGHT IT BACK — AND ONE SONG OFF IT SAT AT NO. 1 FOR FIVE WEEKS. Near the end of his Mercury deal, Toby was told the record he’d made didn’t have the hit they wanted. He talked his way out, paid to own the songs, and took them to DreamWorks. Even there, nobody wanted “How Do You Like Me Now?!” as the first single. Radio had gone female-driven, they argued; a man couldn’t sing that line to a woman. So the ballad “When Love Fades” went out instead, and it never cracked the Top 40. Toby quit waiting on them and picked up the phone himself, working down a list of about 30 radio programmers. Whatever he said on those calls, the label’s plan didn’t survive the week. The song went to No. 1 and stayed five weeks. Billboard named it the top country song of 2000. So what does a man say to 30 strangers that his own label wouldn’t say for him?