In the early 1990s, Toby Keith rolled into Nashville armed with a pocketful of songs and an overflowing cup of ambition. It took him a couple of albums to get there, but by the early 2000s, he was riding high in the charts as one of the biggest names in modern country. He might not be the smoothest or most subtle operator in town, but when it comes to beer, barrooms and heartbreak, there’s no one to touch him. Here, we look back at some of his biggest hits and misses as we rank all the Toby Keith albums from worst to best.
19. Drinks After Work
If Drinks After Work has a problem, it’s that it’s too desperate to be a hit. By 2013, Keith was still outselling most of his peers 2 to 1, but his grip on the top of the charts was starting to loosen. In an effort to claw his way back to the top, he created a frothy, chipper album that sounds like he’s trying to play the game and not upset his audience, rather than truly be himself. It’s by no means a terrible album, but it’s some way short of his best.
18. 35 MPH Town
Like its predecessor, Drunk Americans, 35 MPH Town cares a little too much about being a hit than it should. But despite the occasional whiff of desperation, it’s still an enjoyable record for the most part, with Good Gets Here and the slyly humorous Every Time I Drink I Fall in Love standing out as the chief highlights. Released in October 2015, the album hit number 14 on the Billboard 200 and number 2 on the country charts.
17. Peso in My Pocket
In 2021, Keith released his latest album, Peso in My Pocket. A lively, humorous album that finds Keith jumping from the electronic-inflected pop of Old School to the bawdy, bluesy rock Old Me Better with ease, it’s a hugely rewarding listen, even if it does come with the occasional clunker (Happy Birthday America, we’re looking at you).
16. American Ride
In comparison to the swaggering bravado of his previous album, Keith adopts a sweeter, softer approach to American Ride, showing a rarely seen vulnerable side on songs like Are You Feelin’ Me. It still has its rocking and rousing moments, but it’s the quieter moments that hold the album together. Chief highlights include Ballad of Ballad and Cryin’ for Me [Wayman’s Song]. Released on October 6, 2009, it reached number 3 on the Billboard 200 and number 1 on the country charts.
15. Blue Moon
He may be best known for his blue-collar drinking anthems, but there’s always been more to Keith than beer and bars. On his third album, he showcases his romantic side, sprinkling the tracklist with lovesick numbers like Me Too, A Woman’s Touch, and Does That Blue Moon Ever Shine on You. It’s tender, but not cloying, and while the overall tone is more downbeat than his usual sound, it does a fine job of showing off his winning vocals. Released in April 1996, Blue Moon hit number 51 on the Billboard 200 and number 6 on the Top Country Albums chart, eventually certifying platinum.
A year after creating ripples with his self-titled debut album, Keith was back with his second album, Boomtown. Although he prefaced the album with a disclaimer saying he’d only had a year to write the songs (whereas he’d had a “lifetime” to perfect those on his debut), it’s still a remarkably strong effort, with an excellent balance between traditional country and pop that seems uncontrived, yet still tailor-made for radio. Released in September 1994, the album hit number 8 on the country charts and number 46 on the Billboard 200. Its singles, which include the number one hit Who’s That Man, all cracked the top 20. The album has since certified platinum after selling over 1 million copies in the US alone.
13. That Don’t Make Me a Bad Guy
On 2007’s Big Dog Daddy, Keith adopted a back-to-basics approach. Its follow-up, That Don’t Make Me a Bad Guy, takes the approach even further. A bluesy roadhouse album with a lean, mean tracklist and a brawny swagger to the performances, it’s an undiluted pleasure. Released in October 2008 as Keith’s twelfth studio album, it reached number 5 on the Billboard 200 and claimed the top spot on the country chart, eventually certifying gold.
12. Big Dog Daddy
If you weren’t a fan of Toby Keith before listening to Big Dog Daddy, this isn’t the album to convert you to the cause. But Keith is a man who’s not afraid to be himself regardless of what other people think, and on his stripped-down, back-to-basics eleventh studio album, he reveals himself to be a remarkable songwriter with a keen artistic vision and the ability to wield a hook like a pirate. Released June 12, 2007, the album debuted at number one on both the country charts and Billboard 200.
11. Honkytonk University
Described by the LA Times as a “refreshingly honest outing that still maintains a high fun factor,” Honkytonk University might not be cool (any shot at that was lost the moment Keith gave a shoutout to his “boys in Afghanistan and Baghdad City” in Honkytonk U) but its combination of sly, self-deprecating humor, well-crafted songs, and originality makes it essential listening anyway. Released in 2005 as the last ever album issued by Dreamworks before it closed its doors for good, the album reached number 1 on the country chart and number 2 on the Billboard 200.
10. Toby Keith
The first time Keith tried to make it in Nashville didn’t go well. His attempts to get any record labels to listen to his demo were met with blank faces and deaf ears. Dejected, he hightailed it back home. Fortunately, one of his fans had more faith in him than he had in himself. Even more fortunately, that fan happened to be a flight attendant working on the same flight that Harold Shedd at Mercury was taking. They handed him a copy of Keith’s demo, Shedd liked what he heard, and before long, Keith was back in Nashville with a record contract in hand and the idea for an album in mind. Released in 1993, that album took Keith to number 17 on the US Top Country Albums and number 1 on the Heatseekers Albums chart. A strong debut with an equally strong set of songs (including his breakthrough hit, Should’ve Been a Cowboy), it was obvious at even this early stage that Keith was destined to be a superstar.
9. Dream Walkin’
Commercially, Dream Walkin’, Keith’s fourth studio album, didn’t fare as well as his previous albums, reaching number 8 on the country charts, number 107 on the Billboard 200, and becoming his first album not to certify platinum. Yet it deserved every bit as much attention as its predecessors. It’s a mellow, more laid back affair than usual, but while it’s hard not to long for livelier material (especially considering how excellent the few upbeat numbers like Jacky Don Tucker (Play by the Rules Miss All the Fun), I Don’t Understand My Girlfriend, and She Ran Away with a Rodeo Clown are), Keith’s resonating vocals make even the smoothest tracks irresistible.
8. Pull My Chain
Pull My Chain, Keith’s sixth studio album, is where things really began to change for the singer. The sly humor and bravado he’d taped into on its predecessor, 1999’s How Do You Like Me Now?!, are out in force, resulting in a big, bold album that struts and swaggers its way through the wry, slyly clever tracklist with style. Keith sounds more confident than ever, as willing to turn his hand to the mellow delights of I Can’t Take You Anywhere as to the rollicking cover of Dave Loggins’ Pick ‘Em Up and Lay ‘Em Down. Released in 2001, the album hit number 1 on the country charts and cracked the top ten of the Billboard 200, eventually certifying multi-platinum. Each of its singles, meanwhile, were number one country hits.
7. Ballad in the Gun
Keith’s fourteenth album, Bullets in the Gun, became his first album not to produce a single top 10 single on the country charts. It was far from a commercial disappointment, however, peaking at number 1 on both the Billboard 200 and country charts. Although it has its down and dirty moments, it swings rather than struts, imbued with the easy confidence of an artist who knows his MO and isn’t afraid to deliver it. A tight, lean album with almost no excess fat, it’s a must-listen.
6. Hope on the Rocks
In 2012, Keith delivered another deeply satisfying album in the shape of his sixteenth studio record, Hope on the Rocks. Some critics didn’t like the focus on booze, barrooms, and heartbreak, but it’s done so well, and with such wry humour, it’s hard to grumble. Lean, well crafted, and with an impressively consistent tracklist, it makes an excellent addition to Keith’s catalog. Released in October 2012, it reached number 6 on the Billboard 200 and number 3 on the country charts.
5. Clancy’s Tavern
By the time Keith released Clancy’s Tavern in October 2011, his days of being country’s freshest and hottest new talent were well and truly behind him. And it shows. There’s no attempt to reinvent the wheel, no attempt to prove himself, no attempt to step outside his comfort zone and show off a new side of his talent. Which is just as well – for an artist of Keith’s caliber, there’s absolutely no shame in letting the younger guys worry about being radical while they stick to doing what they do best. A superbly solid outing with a relaxed vibe and dependable tracklist – everything, in a nutshell, that fans want and expect from Keith.
4. Shock’n Y’all
Not everyone was a fan of Shock’n Y’all on its release in 2003. Rolling Stone treated it to a withering review and a score of 2/5, while E! Online remarked that “If he approached these songs with the slightest hint of subtlety, he might get his point across, but he’s happy just hammering everyone with his trailer-park politics.” Ultimately, it’s not an album for everyone. But while it might be easy to dismiss the artist as a jingoistic redneck and the album as rightwing propaganda, doing so would miss the point. Keith isn’t on a mission to convert the world to his point of view, and neither is he trying to push an agenda. He’s just an oversized character trying to create a gutsy, slyly humorous album that might be as polite as a giggle at a funeral, but is too much fun for it to matter. Which is exactly what’s he done.
3. White Trash With Money
In 2006, Keith released his tenth studio album and his first to be issued by his own Show Dog Nashville label. A number 2 hit on both the Billboard 200 and country album charts, it was met with a warm reception from critics, with Rolling Stone describing it as “an arena-ready collection of jokey rockers and sad-cowboy ballads that’s as immaculate and assembly-line sturdy as a new SUV.” A creative, well-crafted album infused with Keith’s trademark sly humor, it ranks easily among his best-ever albums.
2. How Do You Like Me Now?!
After drifting toward mellower, more romantic ballads on his previous two albums, How Do You Like Me Now?!, his fourth album and first with new label Dreamworks, finds Keith shaking loose and getting rowdy. There’s still a good sprinkling of softer, sweeter moments like Heart to Heart (Stelen’s Song) and romantic ballads like When Love Fades, but this is the album that gave us Toby Keith the Showman – or, as All Music puts it, “the big, bad outlaw who hides a big, soft heart.” The strut and swagger he’d perfect on his later albums are still in their embryonic stage, but the seeds of the persona that would make him a mega-star over the coming few years are all in place.
If Pull My Chain, Keith’s sixth studio album, was a hit, its follow-up, the spectacular Unleashed, was an even bigger one. Released in July 2002, the album spawned four hit singles (three of which (Courtesy of the Red, White and Blue (The Angry American), Who’s Your Daddy, and the Willie Nelson duet Beer for My Horses) reached number one), and became Keith’s first album to reach the number one spot on the Billboard 200. It’s since been certified 4x platinum in the US after selling over 4 million copies.