A prominent CountryMusic singer, Toby Keith Covel was born July 8, 1961. He started out rather strongly on the Mercury label, sending his debut single "Should've Been a Cowboy" to #1. This song went on to become the most-played country song of the entire 1990s, but Toby proved to be no OneHitWonder. For most of the rest of the decade, he stayed with Mercury, landing hit after hit with remarkable consistency — between 1993 and 1998, only one of his singles failed to make Top 10. Among his biggest hits in this timespan were several ballads, such as "Wish I Didn't Know Now", "Who's That Man", "Does That Blue Moon Ever Shine on You", and "Me Too", with only "You Ain't Much Fun" hinting at the swagger to come in his later years. Keith then fell victim to ExecutiveMeddling. He had recorded an album for Mercury, but they only liked two tracks, which were both put on a GreatestHitsAlbum. After another album's worth of material was rejected too, he terminated his contract with Mercury in 1999.

A change to Creator/DreamWorksRecords initially flopped, with his first single for the label not even cracking Top 40. But at his insistence, it was withdrawn for one of the songs Mercury had rejected, "How Do You Like Me Now?!", which went on to become a six-week #1 smash and the biggest country hit of 2000. For the next five years, almost everything he released topped the charts and saw considerable crossover success. It was also at this point that he developed his more macho, swaggering style with edgier material such as the CountryRap "I Wanna Talk About Me" and the playful "Who's Your Daddy?", but the sensitive side never went away either, as seen in "You Shouldn't Kiss Me Like This" or "My List". Along the way, he hit big with the controversial "Courtesy of the Red, White & Blue (The Angry American)" and the Music/WillieNelson duet "Beer for My Horses", which made Nelson the oldest country act to have a #1 hit.

After [=DreamWorks=] records closed in 2005, he seamlessly moved to his own label, Show Dog Records (now part of Show Dog-{{Universal}} Music). Although the hits have slowed some, he still managed to get a few more chart-toppers independently. Keith also scored a surprise viral crossover in 2011 when he made a video for "Red Solo Cup", which then dovetailed into radio airplay, but momentum since has slowed greatly.

Keith also owns several business ventures, including the Toby Keith's I Love This Bar & Grill restaurant chain (named after one of his songs) and a line of mezcal.

!!Tropes present in his work:
* AffectionateParody: He wrote a satirical song "I'll Never Smoke Weed with Willie Again", which he sings in Music/WillieNelson's SignatureStyle at concerts.
* AnimatedMusicVideo: The video for "American Ride" is done in a style similar to Website/JibJab.
* AntiChristmasSong: "Jesus Gets Jealous of Santa Claus". Which was co-written by one Music/KeithUrban well before he came famous in the US.
* ArtisticLicenseAnimalCare: Averted. "Beer For My Horses" seems like this, but it actually has a lot of basis in reality. Horse breeders have always given horses beer (Guinness is the preferred brand) as an appetite stimulant. The amount of alcohol in a bottle of Guinness, which is about enough to make a 150-pound man feel pleasantly mellow, will do nothing to a horse which weighs ten times as much and naturally produces huge amounts of enzymes that break down alcohol. The ingredients in beer (grains, hops, yeast and water) are all things a horse will gladly consume on its own, given the chance.
* BadassBoast: Played with on "As Good as I Once Was": The narrator admits that he can't be a badass all the time, but he is put in situations where he still shows that, when pressed, he has at least some of his badassery left ("I ain't as good as I once was / But I'm as good once as I ever was").
* TheBartender: The narrator in "Hope on the Rocks" is a bartender who professes to be a confidant for those who need to [[DrowningMySorrows drown their sorrows]].
* {{Bowdlerize}}: Oddly, most radio stations had no issue with him singing the word "ass" in "Courtesy of the Red, White, and Blue", but that word ''was'' edited out of "American Ride" (which changed it to "Daddy works his ''can'' off") and muted on "Red Solo Cup".
** "Red Solo Cup" also changed "And you, sir, do not have a pair of testicles" to "pair of ''vegetables''", presumably for RuleOfFunny.
** The chorus to "Drunk Americans", which occurs three times, has the line "we don't give a rat's ass". It was originally muted all three times for the radio edit, but a later version changed the first and third instances to "we don't care, we don't ask" and the second to "we don't judge, we don't laugh."
* BrokenWinLossStreak: Only three times in his career has he hit a point where he didn't even make Top 40 on the country charts. The first was in 1999, just as he was leaving Mercury and had put out two sides for a GreatestHitsAlbum. The second of those, "If a Man Answers", stalled at #44. (Although only two singles prior, "Double Wide Paradise" only ''barely'' kept the streak alive, as it stopped right at #40.) And just as he moved to [=DreamWorks=], he released "When Love Fades", which was moving slowly on the charts. It also ended up peaking at #44 because he asked that it be withdrawn and replaced with "How Do You Like Me Now?!", which went on to become the biggest country hit of 2000.
** Despite his popularity fading somewhat over the latter half of the 2000s (mostly), Keith was still at least hitting Top 20 with remarkable consistency. Then came the late-2013 release "Shut Up and Hold On", which peaked at #48, his lowest chart showing ever.
* ChristmasSongs: He's recorded two holiday albums thus far, ''Christmas to Christmas'' in 1995 and ''A Classic Christmas'' in 2007. The former was entirely original compositions, while the latter was a DistinctDoubleAlbum of covers: secular material on the first, hymns and carols on the second.
* CoolButStupid: His reasoning behind recording "Red Solo Cup" (an ode to the plastic cup and its use in drinking, frat parties, etc.) was that it was both the stupidest and most awesome song he'd ever heard.
* CountryRap: "Getcha Some" and "I Wanna Talk About Me" are both examples.
* DooWopProgression: The verses to "Big Blue Note", despite being spoken, have this progression played by the backing instruments.
* DrowningMySorrows: "Get Drunk and Be Somebody" and "Get My Drink On".
** Inverted on "Hope on the Rocks", where he's the bartender observing the many folks who come in to drown their sorrows.
* {{Eagleland}}: Some of his songs "Courtesy of the Red White and Blue", "American Ride", "Made in America", etc. after his FaceHeelTurn fall straight into this category. (However, "American Ride" at least [[PlayedForLaughs plays it for laughs]].)
* EarlyInstallmentWeirdness: His Mercury-era material is a lot more downbeat and reliant on ballads than the swaggering, patriotic personality he soon became known for upon moving to [=DreamWorks=]. In fact, his first [=DreamWorks=] album, despite containing his biggest hit in "How Do You Like Me Now?!", still contains a lot of old-style ballads and none of the swaggering patriotism.
* [[HeelFaceRevolvingDoor Face-Heel Revolving Door]]: Toby Keith pulled the musical equivalent a few years back. His music used to be clean and family-friendly, but for the last several years he's taken on a "bad boy" image and run with it, along with lighthearted, tongue-in-cheek music videos accompanying them, starting with low-level GettingCrapPastTheRadar ("Getcha Some") and gradually progressing to the point where just about any new song from him sounded like pure Straw Conservative propaganda, was a blatant exercise in CrossesTheLineTwice, or both. Somewhere around his departure from [=DreamWorks=], he began to soften again, with occasional exceptions such as "American Ride," which at least had the decency to lampoon both ends of the political spectrum.
* FishEyeLens: Used extensively in the video for "I Wanna Talk About Me", replete with {{Undercrank}}.
* FutureLoser: "How Do You Like Me Now?!" plays with this trope, as he's grown up to be a famous musician while the girl he idolized in high school who never gave him the time of day is unhappy with her adult life. The video drives it home even harder than the song alone.
* HelloNurse: The video to his 2005 hit "As Good as I Once Was" features Toby – who had just been badly beaten by a muscleman during a bar fight – trying to pinch the ass of a sexy paramedic. When the nurse turns around and looks, Toby goes into a seizure and loses consciousness; his losing his battle to stay awake is seen from Toby's perspective, as he blacks out with the iris out.
* IdiotBall: Keith's character in the video for "A Little Too Late," wherein he attempts to seal his ex-girlfriend inside a small, walled off room in the basement and leave her for dead ... only to find out he has actually sealed himself in the walled area. (As he tries to apologize in vain, she leaves the basement to call the police.)
* TheLadette: The subject of "Whiskey Girl" (and "God Love Her", by extension).
* ListSong:
** "My List" is a literal example, as it contrasts a to-do list of household chores and a list of things the narrator really wants to do ("Go for a walk, say a little prayer / Take a deep breath of mountain air…").
** "I Love This Bar" is a list of the various types of characters seen at a local bar (e.g. "We got winners, we got losers / Chain smokers and boozers / And we got yuppies, we got bikers / We got thirsty hitchhikers…").
* MisogynySong: "How Do You Like Me Now?!" has been interpreted by some as this.
* MockingSingSong: Played during the fade-out of "How Do You Like Me Now?!"
* PissTakeRap: "I Wanna Talk About Me", and he has a decent flow too.
* PoesLaw: His war-on-Christmas song, "Have I Got a Present for You", which he performed on ''Series/TheColbertReport'', has been treated as if it's actually serious by many, despite promoting murder and generally being as parodic of EagleLand as you can get. There's also the aforementioned "Courtesy of the Red, White, and Blue".
** "American Ride" also got some heat from the politically-minded, but as Keith himself points out, the song lampoons both the left and the right.
* ProductPlacement: "Red Solo Cup" is basically a commercial.
* RecordProducer: He was produced by Nelson Larkin and Harold Shedd on his first two albums, then co-produced with just Larkin on the third. He co-produced with James Stroud from ''Dream Walkin''' through the new tracks on his second GreatestHitsAlbum. Keith has largely produced by himself ever since, with assistance from Lari White (best known for her 1995 hit "Now I Know") on ''White Trash with Money'', bluegrass musician Randy Scruggs on his 2007 Christmas album, and Bobby Pinson on ''35 MPH Town''.
* [[RockstarSong Country Star Song]]: "Honkytonk U" is a firsthand account of Toby's rise to the top.
* SelfPlagiarism: "God Love Her" has a ''very'' similar premise and melody to "Whiskey Girl".
* StrawCritic: "The Critic".
* SubvertedRhymeEveryOccasion: "You Ain't Much Fun":
-->Now, I'm fixin' the sink, and I'm mowin' the grass
-->You even made me a list and I'm bustin' my...
-->Well, all broke down, tail's been draggin'...
* ToplessnessFromTheBack: The video for "Who's Your Daddy?"
* TrailerParkTornadoMagnet: Referenced in "Trailerhood": "When the storm starts gettin' bad and you hear those sirens hummin' / Grab a six-pack and a lawn chair, there's a tornado comin'."
** Which is much HarsherInHindsight considering his hometown of [[http://en.wikipedia.org/wiki/Moore,_Oklahoma Moore, Oklahoma]] was struck by devastating F5 tornadoes in 1999 and 2013. At least half of the town was leveled during both tornado outbreaks and dozens of people were killed (including several schoolchildren).
* TruckDriversGearChange:
** "I'm So Happy I Can't Stop Crying" goes from E-flat to E near the end as the song's tone changes to happy.
** "Lost You Anyway" goes from D to E at the first chorus, and again to F-sharp on the second chorus.
** "Red Solo Cup" goes from A to B on the last chorus.
* UnusualEuphemism: "American Ride" has both "gets her rocks off" and "[[{{Spoonerism}} the fit's gonna hit the shan]]". Also a great example of GettingCrapPastTheRadar; anything that telegraphs more than a mild profanity is usually shunned.
* WrestlerInAllOfUs: A non music example, in the early 2000's Toby made a couple of appearances in TNA Wrestling, culminating with him delivering an impressive looking vertical suplex to Wrestling/JeffJarrett.