[3] Olson decided to be a comedy writer as a boy when he saw comedian Brother Theodore ranting and raving on The Merv Griffin Show.

(According to his agent's press kit, years later when writing for Penn & Teller in Las Vegas, Olson produced comedy bits with Dangerfield and the two became friends.

After two years Olson and Clarke were fired for airing two controversial segments ("News for Negroes" and "The Mentally Challenged Faith Healer" featuring Bobcat Goldthwait).

[11] While staff writer for Rocko's Modern Life, Olson's office was next to that of Stephen Hillenburg, his friend who years later would create SpongeBob SquarePants.

Olson read The Intertidal Zone, an educational comic book hosted by a sea sponge character, which Hillenburg had written and illustrated.

Olson and his writing partner comedian Jeremy Kramer were head writers for Fox's Comic Strip Live, for Screen Actors Guild Awards for three years, and for the animated series The Twisted Tales of Felix the Cat.

[15] With Ken Kaufman and Howard Klausner, Olson co-wrote the final draft of the screenplay adaptation of his book for WB under a new title, D-Men.

Olson was a contributing story writer ("Additional Writing By") and songwriter for Disney's TV film Phineas and Ferb the Movie: Across the 2nd Dimension.

[10] As an occasional actor, Olson has guest-starred in live action sequences in SpongeBob SquarePants ("Mermaid Man and Barnacle Boy V" and "Swamp Mates"), in "Don't Watch This Show" by director-comedian Bobcat Goldthwait, in the documentary When Standup Stood Out by filmmaker Fran Solomita, and on The Tonight Show playing an Indian yogi with comedian Bobcat Goldthwait.

Olson also appears in videos by his friends Garfunkel and Oates, Melinda Hill, Katie Schwartz, Adam Scott Franklin and Rich Dorato.

His satirical songs were regularly featured on many television series, including London Underground (Comedy Central), Rocko's Modern Life (Nickelodeon), Get That Puss Off Your Face (HBO), Camp Lazlo (CN), Penn and Teller's Sin City Spectacular (FX), The Twisted Tales of Felix the Cat (CBS), Phineas and Ferb and Milo Murphy's Law (both for Disney).

Olson has had his songs performed by a diverse list of artists, including Clay Aiken, Chaka Khan, Jack Jones, "Weird Al" Yankovic, Kenny Loggins, Kate Pierson of The B-52's, Fee Waybill of The Tubes, Michael McKean of Spinal Tap, Wayne Brady of Whose Line Is It Anyway?, Jack McBrayer of 30 Rock, Malcolm McDowell, Jaret Reddick of Bowling for Soup, Richard O'Brien of The Rocky Horror Show, French Stewart, Ian McKellen, Joey Lawrence, Ashley Tisdale, Christian Slater, Sheena Easton, Carmen Carter, Jemaine Clement of Flight of the Conchords, Robbie Wyckoff, Tom Kenny of SpongeBob, Allison Janney, Big Bad Voodoo Daddy and his daughter, singer-songwriter Olivia Olson.

[19] Olson's encyclopedic satire Encyclopaedia of Hell is published by Feral House (July 2011);[20] the film rights were bought by Warner Bros. through producer Andrew Lazar for Mad Chance.