Wild and free like a Rolling Stone,
They gotta love takes 'em higher than the Eagles,
Ain't life such a sweet, sweet song.
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 would continue recording, 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".
Diffie died on March 29, 2020 after being stricken with COVID-19, or coronavirus.
- 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.
- The Cameo: The video for "Bigger than The Beatles" has a couple of shots of a Beatles tribute act singing the "Yeah yeah yeah yeah!" line towards the end of the song.
- 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.
- Comically Missing the Point: From "I'm in Love with a Capital 'U'": "Every time the teacher said pi R squared, all I could think about was going to lunch."
- 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.
- Do Wrong, Right: In "John Deere Green", the townspeople take issue not with the fact that a teenager vandalized a water tower, but that he used green instead of red paint to declare his love for a girl.
- '80s Hair: Rocked a mullet in the early part of his career in the 90s. He toned it down as the decade came to a close but always wore his hair slightly longer at the back than fashionable.
- 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 Smokey's Bar who decides to go for a fling. He calls his wife with a lie about working late, who calls her sister to come over for consolation, whose boyfriend goes off to buy a beer, whose pickup is stolen by teenagers on a joyride... The eventual chain of chaos ends in the cops calling the mayor because they can't find the Chief of Police — who as it turns out, is still at Smokey's Bar.
- Homesickness Hymn: Diffie's breakout song "Home" offers up a cornucopia of the narrator's memories of home growing up, and expresses longing for that simpler, more comforting time.
- 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.
- Shout-Out: "Bigger than The Beatles" (which has the ending "Yeah yeah yeah yeah!" from "She Loves You" line incorporated into the song) also has lyrics referencing Elvis Presley, The Rolling Stones and The Eagles.
- 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 puts "Billy Bob Loves Charlene" on a water tower in the titular paint. The sign of their love remains visible well after they've married, despite numerous attempts to cover it up.Now more than once, the town has discovered painting over it ain't no use
There ain't no paint in the world that'll cover it, the heart keeps showing through