- Dick Masterson - A big man with a small face and a smaller ideal government.
- Sean, The Audio Engineer - Ass farmer, dope smoker. Handsome as fuck.
- Asterios Kokkinos - A paradoxically loud and sneaky Greeky.
- Life Coach - A second amendment man. Starts fights with murderers.
- Kian Magaña - Dick's lawyer, wannabe ladies man
- Allegra Ringo - A podcaster, dog lover, and probably a feminist blogger.
- Denzel - The ho-host with the mo-most. Good taste in music.
- Dick's Man - Dick's Man Steve. Married at Burning Man, witnessed by a cat.
- Handy Randy - A Hollywood big shot than takes great pleasure in crushing the dreams of people that posses the same coloured skin as Denzel.
- Harmful Opinions - Youtube commentator
- Joan Ford - Like, a UCB Tournament of nerds regular?
- Joe Starr - Hollywood Superstarr, writer for Screen Junkies or something.
- Joey Clift - Wrestling fanatic, and another guy with a podcast.
- Larry Bleidner - A velvet-voiced father with a "take no shit" attitude.
- Layc Nichole - News babe with a large forehead. Reserved for Sean.
- Lenora Claire - Tits.
- Lowtax - Devours hamburgers, hates trees, gets in fights with angry Germans.
- Madcucks - Our very own dull-voiced master satirist.
- Mark David Christenson - Host of the podcast I will Watch Anything Once, another guest that attempts comedy.
- Mike Cernovich - Angry lawyer, pharmaceutical enthusiast, aggressive tweeter.
- Nathan Buckley - Glues pretzels onto his baseball cap, rides generators like they're a woman.
- Null - Creator of Kiwi Farms, helped develop 8chan. Milk enthusiast.
- Peach Saliva - Streamer, funnier than Asterios the career comedian.
- Robin Higgins - A comedic chemist that utilizes the power of chemistry to forcefully make others laugh.
- Sam Hyde - School shooter and terrorist. Had his TV show taken down by social media terrorists.
- Jamie Lynn Hughes - Fitness Model and IRC Degenerate
Call in / Rage board
- Dustin - The Facebook Meme Man, "Chief Dickhead" and "beloved" return caller.
- David Clegg - Case for "People who like to sleep" being a problem, lonely. alleged paedophile, Hulk Hogan and Asterios impressionist.
- Lettuce Jones - Antagonistic leafy jailbird of mysterious race. Likes books. Likely to be "Doing the shanking".
- Izzy Nobre - Brazilian podcaster, ringer, really big fan of TBPITU. Was the reigning champion of the Rage Lottery until it was canned.
- Slag Tess - Madcucks' girlfriend, misses Sean. Probably sleeping with whatever our satirical Rucka ends up getting called.
- Spinach Smith - Arch rival to Lettuce Jones, wants to be the next co-host to the Dick Show.
- Wauterboi's bird - SQUAK
- Chinese Tony - hates life. Wants to die. Also Chinese.
- Spicy Tony - conned out of a job. Not Chinese.
- Maxwell Kimball - Some 18 year old guy that was going to beat up Daivd Clegg in real life.
- Phteven - A down to Earth guy that just happens to get mixed up in the weird world of furrys, trans and polyamorous fuck nests.
- Frank the Tank - Spokesmen for the suicide clique of Dickheads.
- WarOfTheFanBoys - Moderator of /r/The_Donald, has an angel on the table.
- Hazencruz - - Raided Maddox's Twitch stream, has a thick Southern accent.
- Thomas McCoy - A filmaker that's an Autist, how original.
- Sovash - Official Representative of Reddit
- Consuelo - A proud Mexican gardner and podcaster.
Never heard directly on the show but very much still Characters within TDS Universe.