His material was often topical in nature, addressing the political climate with his own libertarian views. When he wasn't doing that, he was poking fun at himself or the South, or bringing out the guitar to do some novelty songs.
Wilson got his start as a songwriter, including cuts for country comedy duo Pinkard & Bowden and Jeff Foxworthy's "Redneck 12 Days of Christmas". Originally, he recorded for the small Southern Tracks label before moving to Capitol Records in 1999. Some of his most famous songs include "Garth Brooks Has Ruined My Life", "Booty Man", and "Dale Darrell Waltrip Richard Petty Rusty Awesome Bill Irvin Gordon Earnhardt Smith... Johnson Jr." These, and many others, were in regular rotation on The Bob & Tom Show.
He continued to tour and record until shortly before his death from a heart attack on February 27, 2014. Soon afterward, the hosts of The Bob & Tom Show held a tribute concert in his honor.
Albums
- Waking Up the Neighborhood (1994)
- Tough Crowd (1995)
- Low-Class Love Affair (1995)
- Songs for the Musically Disturbed: His (Almost) Greatest Hits (1996)
- Tuned Up (1997)
- It's a Sorry World (1999)
- Road Comedy 101 (1999)
- Gettin' My Mind Right (1999)
- Hillbilly Homeboy (2000)
- I Should've Married My Father-in-Law (2001)
- Certified Aluminum: His Greatest Recycled Hits, Volume 1 (2002)
- Super Bad Sounds of the 70's (2003)
- The Real Twang Thang (2005)
- Church League Softball Fistfight (2005)
- But I Could Be Wrong (2007)
- Mr. Wilson Explains America (2009)
- Caffeine Wired, Nervous & Pale (2013)
This is Tim Trope Wilson, and the Trope Callers. They call it: Trope Man!
- Chart Displacement: His most famous song "Booty Man" didn't chart, and "Dale Darrell Waltrip Richard Petty Rusty Awesome Bill Irvin Gordon Earnhardt Smith… Johnson, Jr." wasn't a single. Both of these are considerably more famous than his highst chart entry, "The Ballad of John Rocker".
- Clumsy Copyright Censorship: To get the Chuck E. Cheese's song on an album, he had to name it "Chucky Cheese H*ll" and put a warning on the album that the song was not approved by Chuck E. Cheese's.
- Country Rap: Parodied on "Hillbilly Homeboy", which uses a hip-hop beat to back up a story about a displaced southern boy in a stereotypically urban neighborhood.
- Deep South: Like many Southern comedians, he joked about Southern stereotypes regularly.
- Early-Bird Cameo: One of his first gigs was writing material for country music parodists Pinkard & Bowden.
- Episode on a Plane: “Super Bad Sounds of the 70s” is set on The Shoals Plane.
- Everything Is an Instrument: He plays a pair of scissors on "Haircut Malpractice".
- God Before Dogma: The preacher from "The First Baptist Bar & Grill" versus the traveling ministry who says his move to the eponymous restaurant after his church burned down is fraught with sin. Preacher points out that they've saved more souls in here than they ever have, and the only person the traveling ministry saved last year was the guy who burned his church down.
- I Want My Jetpack: "Where's My Jetpack" of course.
- Issue Drift: I Should've Married My Father-in-Law is pretty heavy on his right-wing politics, as seen in "Hollywood" (which insinuates that only liberals can survive in Hollywood) and "Brady Bill, Gunfighter Without a Gun" (a Western-themed shootout song lampooning the Brady Handgun Violence Prevention Act
). - The Münchausen: The "Uncle BS" skits, in which the uncle in question recounts a blatantly made-up story about where he was on a certain day in time.
- No-Hit Wonder: He never had a major chart hit, but still had a nearly two-decade recording career.
- Obsession Song: “Booty Man” is about the said character saying every type of booty.
- Parody Commercial: The last track on Hillbilly Homeboy is one for "Love Songs for Losers".
- Phony Veteran: "He's My Brother-in-Law": "He tries to blame it all on Vietnam / But he wasn't there, he was twelve in '74".
- Punny Name: Corny Donelious is a backward version of Don Cornelius.
- Sdrawkcab Speech: “Corny Donelious”
- Shout-Out: The Shoals Plane is a parody of Soul Train.
- Sound-Effect Bleep: "Darryl Stokes, that dumb sonofa [BLAM], almost shot Santa Claus."
- Stuffy Old Songs About the Buttocks: "Booty Man", Played for Laughs.
- Subverted Rhyme Every Occasion: Occurs in "Love Songs for Losers": "Chuck, Chuck, Chuck, Chuck / I think she finally wants to fffffffffforget about yesterday."
- Suck E. Cheese's: "Chucky Cheese Hell" is sung from the point of view of a bouncer at a Chuck E. Cheese's.
- Ugly Guy, Hot Wife: One of the "100 Things Every Man Ought To Know" is "If you say 'I do.' be the ugly one."
- Word Salad Lyrics: “Booty Man” is all the random types of booties which are words.
