A native of Tulsa and a former foundryman, he was divorced and bankrupt by the time he moved to Nashville in the mid-80s. An encouter with producer-songwriter Bob Montgomery led to him signing to Epic Records, who released his debut album A Thousand Winding Roads in 1990. Lead single "Home" made him the first artist to send a debut single to #1 on all three of the major country music charts of the time (Billboard, Radio & Records, and Gavin Report). Followup albums Regular Joe, Honky Tonk Attitude, Third Rock from the Sun, and Life's So Funny found his sound refining into a commercially successful product.
Although the hits dried up by the end of the decade, Diffie has continued to record to this day, with later albums focusing more heavily on ballads. He also had a stray hit as a songwriter in 2005 when Jo Dee Messina covered his "My Give a Damn's Busted".
Diffie was heavily referenced in Jason Aldean's 2013 hit "1994".
- A Thousand Winding Roads (1990)
- Regular Joe (1992)
- Honky Tonk Attitude (1993)
- Third Rock from the Sun (1994)
- Mr. Christmas (1995)
- Life's So Funny (1995)
- Twice upon a Time (1997)
- Greatest Hits (1998)
- A Night to Remember (1999)
- In Another World (2001)
- Tougher than Nails (2004)
- Homecoming: The Bluegrass Album (2010)
- All in the Same Boat (with Aaron Tippin and Sammy Kershaw) (2014)
Tropes present in his work:
- Album Title Drop: A Thousand Winding Roads is name-dropped in lead single "Home".
- Black Comedy: In "Prop Me Up Beside the Jukebox (If I Die)", the narrator asks for his corpse to be placed beside the jukebox with a "stiff drink" in his hand.
- Cerebus Syndrome: A Night to Remember was more driven by smooth soft ballads, with none of the novelty sounds of his 90s albums.
- Christmas Songs: Mr. Christmas, issued in 1995, features the comedic track "Leroy the Redneck Reindeer", about Rudolph's redneck cousin Leroy who fills in for a sick Rudolph one Christmas.
- Distracted by the Sexy: Present in "Bigger than the Beatles". A waitress in a bar and a musician who performs in the bar are very much in love. Sometimes she forgets an order because she's thinking about how handsome he is, and sometimes he forgets to sing a chorus because he's thinking about how beautiful she is.
- Early-Bird Cameo: Before having any hits of his own, he wrote and sang backing vocals on Holly Dunn's late 1989-early 1990 hit "There Goes My Heart Again".
- Hoist by His Own Petard: The chain of events in "Third Rock from the Sun" is started by a man in a bar who calls his wife to tell her that he's working late, when in reality he's having an affair with another woman. The wife calls over her sister for consolation, but the sister's boyfriend drives off to buy beer. In the process, the boyfriend's car is stolen by teenagers, who crash it into a semi truck and cause a power outage, which freaks out a waitress who calls the cops. The cops then call the mayor because they can't find the sheriff — who as it turns out, is hiding from his wife at the bar.
- Honest John's Dealership: The subject of "If the Devil Danced (In Empty Pockets)", which is about the narrator getting taken advantage of by the owner of such a dealership called "Diablo Motors".
- Porn Stache: A part of his look for most of his peak years.
- Rearrange the Song: Both "John Deere Green" and "Third Rock from the Sun" were rearranged for the radio edit: the former had cleaner instrumentation with some of the repeats removed, and the latter took out a couple instruments and a Lyrical Cold Open.
- Spelling Song: Played straight with "C-O-U-N-T-R-Y", but subverted with "I'm in Love with a Capital 'U'":You got me feeling so G-U-D
It's more better than I thought it could be
Girl, you taught me things that I never learned in school
I'm in love with a capital "U"
- Subverted Rhyme Every Occasion:
Well the waitress never leaves you with a half-empty glass
- In "Honky Tonk Attitude":
And every girl's on the dance floor shakin' her... Well...
I'm runnin' this shovel way down in a ditch
- "Down in a Ditch" pulls off a double-subverted rhyme:
When you're down in a ditch, it's a son of a gun
Any fool knows you'll never get rich
When you're down in a ditch in the Tennessee sun
- Sweetie Graffiti: In "John Deere Green", a man named Billy Bob paints "Billy Bob Loves Charlene" on a water tower. The couple marries and the sign of their love remains visible, despite the town's attempts to cover it up.