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Toby Keith - 35 Biggest Hits Review
Posted by Mitch Michaels on 05.12.2008



My Story
There are few hit machines more consistent in country music than Toby Keith, and yet he seems to have to re-prove himself with each album. There have been several moments in Keith’s career where he could have faded into obscurity (even as recently as 2006, when he jumped from DreamWorks to his own Show Dog label), but each time he’s battled back with big hits and well reviewed albums. How does he do it? He’s simply one of the best songwriters in Nashville. And this latest hits collection, spanning his career from 1993 to 2006, aims to put that on display. Will it succeed?

His Story
Toby Keith was born in a small town in Oklahoma and spent his later youth in the suburbs of Oklahoma City. Keith first learned to play guitar before he’d even reached middle school, but upon graduation, he went to work in the oil industry. At 20, he formed a little side band called Easy Money, and they spent the weekends playing in local bars.

In 1982, Oklahoma’s oil industry hit a major slump and Keith, a guy who’d steadily worked his way up the ladder towards management, found himself out of a job. Without a college degree, Toby fell back on his high school football experience, playing semi-pro for Oklahoma City’s Drillers and continuing his Easy Money gigs on his off time. In 1984, Keith decided that the pros wouldn’t be calling anytime soon, so he decided to put his heart and soul into Easy Money, seeking a full time music career. The band found some moderate success in the Oklahoma and Texas area. That same year, Keith married his wife Tricia.

Toby Keith told himself that he would give up on music if he didn’t have a recording contract by the age of 30. In 1993, at the age of 32, Keith finally gave up busking and handing out demos in Nashville, supposedly for good. He returned home to Oklahoma, but fate intervened. A copy of Toby’s demo found its way into a Mercury Records executive lap by way of a flight attendant/Toby Keith fan. The exec signed Keith on the spot following a show in Oklahoma.

In mid-1993, Mercury Records released Toby Keith’s self-titled debut. The lead single, “Should’ve Been A Cowboy”, became a #1 country hit (it even spent a brief time in the Billboard Hot 100). Three more Top 5 country singles followed and Toby Keith became a Top 20 country album. What a difference six months had made!

Keith’s debut album was certified platinum in October of 1994. The next month, his second album, Boomtown, was released on Polydor Records. The album produced three more Top 10 hits, including the #1 separation ballad “Who’s That Man” and the #2 duet with Sting “I’m So Happy I Can’t Stop Crying”. Boomtown stalled out shy of a million copies, but Keith followed up swiftly with 1996’s Blue Moon. His third release reached #6 on the country charts (and #51 on the Billboard 200), Keith’s best chart position yet. It was also his second platinum album, thank to the strength of the #1 hit “Me Too”, as well as a couple other Top 10 country singles.

Keith managed to survive the closing of the Polydor label and jumped back to Mercury Nashville in 1997. For his fourth album, Keith teamed with notable producer James Stroud, giving him a more impactful sound and a slightly more polished production. The tune-up worked well. Keith’s fourth record, Dream Walkin’, was another Top 10 country gold record, producing another steady pair of Top 5 singles.

With four albums under his belt now, Toby returned to the studio to work on a follow-up a seasoned vet. Unfortunately, Keith and Mercury did not see eye to eye when it came to his new album. Toby got fed up with the label intervention, purchased the rights to the material he’d recorded and began searching for a new record company. Keith’s final album with Mercury was 1998’s Greatest Hits, Vol. 1, which has since gone double platinum.

Keith finally settled at DreamWorks in 1999, when he released his fifth album. How Do You Like Me Now?! was a new beginning for Keith. It featured a much brasher style of songwriting, featuring honky-tonk songs and love songs each blended with a bit of attitude. Not only did the record produce two #1 country hits (the title track and “You Shouldn’t Kiss Me Like That”), the songs also put Toby into Billboard’s Top 40 for the first time. It seemed that after six years and a truck load of country hits, Toby Keith was just getting warmed up.

The new decade has proven fruitful for Toby Keith. How Do You Like Me Now?! went platinum and earned the singer a whole slew of industry awards. Keith started appearing on national TV, including a stint as a phone company advertiser and even in a “Dukes Of Hazzard” TV movie. In 2001, Keith released his hotly anticipated sixth album, Pull My Chain. The album debuted at #1 on the country charts and #9 on the Billboard 200, a first for Toby Keith. In another first, Chain yielded three #1 country hits, which were also all Top 30 on the pop charts (“My List”, “I’m Just Talkin’ About Tonight” and “I Wanna Talk About Me”). Chain was also Keith’s first record to go double platinum.

Though he had tasted plenty of success since his jump to DreamWorks, nothing compared to Keith’s follow-up single, a flag-waving, chest-thumping response to the 9/11 attacks called “Courtesy Of The Red, White And Blue (The Angry American)”. The song was an instant hit with country and pop audiences. It topped the country charts and peaked at #25 on the Billboard Hot 100. The single has since been certified gold. “Angry American”’s associated album, Unleashed, was released in 2002 to rave reviews. It topped the Billboard charts upon its release and managed to yield another #1 country hit (“Who’s Your Daddy”) and another gold single (“Beer For My Horses”, a duet with Willie Nelson). Keith appeared on even more TV, beginning a long sponsorship deal with Ford and even participated in several TNA wrestling Pay Per Views.

2003’s Shock’n Y’all continued in the formula of its predecessor. It also debuted at #1 on the Billboard 200. The record yielded three big country singles (“American Soldier”, “I Love This Bar” and “Whiskey Girl”, all gold certified #1’s). And, like Unleashed, Y’all has also been certified four times platinum, tying it as Keith’s career best-selling record.

In 2004, as Keith was busy working on his ninth studio album, DreamWorks released the triple platinum Greatest Hits 2, which covered Toby’s material since leaving Mercury Nashville. In spring of 2005, Keith’s proper follow-up, Honkytonk Univeristy, once again flew off the shelves, thanks in part to another gold single, “As Good As I Once Was”. Though not quite the success that his previous two records had been, Honkytonk U kept Keith on the radio and went on to sell over a million units.

But all was not well in the Keith camp in 2005, as he was once again experiencing label problems. Universal Music Group had just purchased DreamWorks Nashville, and Toby saw that as a good time for his exit. He opened his own label, Show Dog Nashville, which released its first album in 2006: Toby Keith’s White Trash With Money. The album debuted at #2 on the Billboard charts (shut out of #1 by fellow country act Rascal Flatts). It was Keith’s first record since the 90’s to not feature James Stroud as producer. The result was hailed as a throwback to the days of outlaw country. Casual fans weren’t quick to embrace it, though. White Trash only took a month to be certified platinum, but at radio, it was Keith’s first record to not yield a #1 single since the 90’s – though it did feature the #2 hit “A Little Too Late” and the #3 “Get Drunk And Be Somebody”. That same year, Keith starred in his first movie, Broken Bridges.

In 2007, Keith returned to the studio to work on his eleventh studio album. It was his first time acting as his own producer. The result was Big Dog Daddy, another gold #1 hit that followed the sound of White Trash. Daddy yielded Keith’s 17th #1 Country hit in “Love Me If You Can”, and another Top 5 single in “High Maintenance Woman”.

2008 is rumored to be a busy year for Keith, with a twelfth studio album, a new movie and soundtrack and a new compilation album in the works.

The Album
On May 6, 2008, Show Dog Records and UMG released 35 Biggest Hits, a compilation of Toby Keith’s highest charting singles from his debut up until his 2006 release White Trash With Money. The album features one new song, too, the single “She’s A Hottie”.


The Band: 7.5
Toby Keith: vocals, producer

Taking a chronological look at Toby Keith’s career, from his self-titled Mercury debut to his current Show Dog Records output is interesting. Not only do you see Keith evolve as a songwriter, but you also see how Nashville production has changed over the past 15 years. Well, that’s not entirely accurate, as come the mid-2000’s, Keith abandoned that sort of thing and took more control over his sound, coming off with a more rootsy feel, harkening back to the outlaw country of the 70’s, if it were filtered through a clean glass anyway.

The songs on 35 Biggest Hits find Keith constantly backed by crack Nashville musicians, and they see him move from just another guy during the early 90’s country boom (could that be referenced in his album-track “Boomtown”?) to an outlier who crooned and paired with Sting, to the flagwaving, John Mellencamp counterpart to his current incarnation as resident crack songwriter/party guy. The sounds change, but the quality of the songs rarely do, as everything is thick and layered. The Blue Moon/Dream Walkin’ material is especially interesting, an era when Keith flirted with pop crossover heaviest.

This all makes the division between discs one and two very visible, as 90’s Keith becomes 00’s Keith, a guy who cared less and less for the country-pop mainstream and more for getting his point across and playing with guys like Willie Nelson. Luckily, the hits are just as strong, as there’s no dip in quality, even as Keith jettisons super producer James Stroud towards the end. With moves like that, something tells me a 30-year retrospective will prove just as intriguing.

The Songs: 9.0
Disc 1:
1. Should’ve Been A Cowboy
2. He Ain’t Worth Missing
3. A Little Less Talk And A Lot More Action
4. Wish I Didn’t Know Now
5. Who’s That Man
6. Upstairs Downtown
7. You Ain’t Much Fun
8. Big Ol’ Truck
9. Does That Blue Moon Ever Shine On You
10. A Woman’s Touch
11. Me Too
12. We Were In Love
13. I’m So Happy I Can’t Stop Crying
14. Dream Walkin’
15. Getcha Some
16. How Do You Like Me Now?!
17. Country Comes To Town
18. You Shouldn’t Kiss Me Like That

Disc 2:
1. I’m Just Talkin’ About Tonight
2. I Wanna Talk About Me
3. My List
4. Courtesy Of The Red, White & Blue (The Angry American)
5. Who’s Your Daddy?
6. Beer For My Horses
7. I Love This Bar
8. American Soldier
9. Whiskey Girl
10. Stays In Mexico
11. Mockingbird
12. Honkytonk U
13. As Good As I Once Was
14. Big Blue Note
15. Get Drunk And Be Somebody
16. A Little Too Late
17. She’s A Hottie

35 Biggest Hits is exactly as advertised, covering Keith’s biggest charting Country songs from his debut until 2006, halfway through releasing singles for White Trash With Money. That means UMG and Keith’s Show Dog lavel got together to bring us EVERYTHING here. I was a little disappointed that nothing from Big Dog Daddy was included, but I can understand not wanting to step on the toes of an album that’s only been around for a year. For a guy who is known for hit singles, a few had to be trimmed. These include “Double Wide Paradise”, which topped out at #40, a pair of singles that missed the Top 40 (“If A Man Answers” and “When Love Fades”) and the #13 2002 single “Rock You Baby”, the most puzzling of the deletions, simply because it charted higher than some tracks that did make the cut, most auspiciously Toby’s not-so-great duet with his daughter “Mockingbird”.

That said, the few tracks that are missing likely won’t be missed, as all of the BIG hits are here. Hell, half of them are #1 singles. Each album is represented pretty fairly, save for White Trash With Money, which only got two tracks. As for the songs, casual listeners who have pigeonholed Toby as the flag waver or the smart ass or the party tune singer will be surprised to find that he’s all this and more. Keith mines several themes in his hits, including wistful nostalgia (“Should’ve Been A Cowboy”, “We Were In Love”), American pride (“The Angry American”, “American Soldier”), honky tonks (“Honkytonk U”, “I Love This Bar”), trucks (“Big Ol’ Truck”), and, of course, love won and lost. Keith is actually best in this category, with great songs about getting together (“Me Too”) and breaking up (“I Wish I Didn’t Know Now”). And of course, the guy knows how to write a country punchline – look no further than “Getcha Some” or “Who’s Your Daddy?” for proof.

In the end, this set is the new definitive Toby Keith collection, as it mines nearly everything from his previously released Greatest Hits CDs (minus a couple of tunes exclusive to those – now that’s smart marketing!), as well as updating them to include Keith’s post-2003 output. Of course, if you’re a Toby Keith fan, you have all of these sets, meaning the only reason to pick up this set is the new single “She’s A Hottie”. The cut, produced by Keith himself – meaning it’s either an outcast from Big Dog Daddy or was recorded specifically for this set – is Keith’s sexiest, for sure, but a little well…check out these lyrics:

“Hottie, she’s a hottie
And just a little bit naughty
Ki-yi-diggy diggy, Ki-yi diggy diggy
Yay hey hey”

Still, it’s got a good feel to it, and is dumb enough to be a huge hit, probably. Still, having Keith’s hits all in one place is the big get here, and it does that exceedingly well.


The 41135 Biggest Hits is the new essential Toby Keith album, featuring all of his biggest and best hits. Everything you could want is here, even a decent new single. Tracks like “Who’s That Man”, “The Angry American”, “My List”, “Does That Blue Moon…” and tons others prove why Toby Keith is one of the best and most versatile songwriters in country today. Hearing the progression of Keith’s 90’s production to his current style is interesting. But not distracting thanks to the chronological ordering. If you’re a Keith fan but haven’t got the albums, pick this up today.
411 Elite Award
Final Score:  8.5   [ Very Good ]  legend


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