Audiences today know Bob Odenkirk as an actor, and specifically as Saul Goodman aka Jimmy McGill in Breaking Bad and its spin-off series Better Call Saul. But before the scam artist lawyer was even a hint of an idea, Odenkirk had a long career as a comedy writer and actor. He was an integral part of the ’90s comedy scene, working alongside modern comedy superstars like Conan O’Brien, Ben Stiller, and Dino Stamatopoulos in the early stages of their careers.

Odenkirk has shown his talent and range as a writer and actor in recent years, proving to audiences that he can play the multifaceted McGill just as well as he can play Charles Manson in a bizarre parody of Lassie. He even hopes to impress audiences in an upcoming green screen rendition of The Room, where he’ll play Johnny — the role originated by Tommy Wiseau — alongside Bella Heathcote, Greg Sestero, Kate Siegel, and Mike Flanagan.

Odenkirk’s work has had an enduring impact on the comedy scene, influencing, directly and indirectly, the work of celebrated comedy duos like Tim & Eric, Tenacious D, and Key & Peele. Looking back on his vast catalog of early work, it’s very easy to see why.

Bob Odenkirk’s Early Career at Saturday Night Live

NBC

Bob Odenkirk loved comedy from an early age, and that passion was always a driving force behind his choices. Before he’d finished college, the young writer decided to pick up and move to Chicago to try making it on the comedy scene. During this time, he’d meet Robert Smigel, the collaborator and friend that helped Odenkirk land his first big gig: writing for Saturday Night Live.

Smigel and Odenkirk brought some of this early work over to SNL, including the one that Odenkirk and others consider his best. The famed “Down by the River” sketch stars Chris Farley as Matt Foley, a downtrodden motivational speaker that uses his own failure as inspiration for his speeches. Foley is loud and obnoxious, but between Odenkirk’s writing and Farley’s performance, the character has an underpinning of pathos that makes him significantly more relatable and hilarious.

Related: The Best Bob Odenkirk Movies and TV Shows

Odenkirk won his first Emmy working for SNL in 1989. During his time there, the writer would also work alongside renowned comedians like Conan O’Brien, David Spade, and Adam Sandler. Odenkirk eventually tired of SNL’s tight deadlines and “safe” content, and he soon made his way out west to find work in Los Angeles.

Bob Moves West

Fox

The comedian didn’t have any trouble finding work. Fox was interested in hiring him as a writer for The Simpsons, but Odenkirk didn’t care for that show’s notoriously long hours. He would, however, help his brother Bill Odenkirk join The Simpsons writing staff from 2004 to 2016. Bob instead took a job with another show that he’d recently become a fan of: Get a Life. After that show ended, Odenkirk joined The Ben Stiller Show as a writer and performer. During his time, he was a part of enduring sketches like “Melrose Heights 9021024026,” “Amish Studs,” “Headslammer’s Ball,” and the aforementioned “Manson.”

The Ben Stiller Show was a place where Odenkirk could be his wacky self among his peers. During this period, the comedian worked with architects of modern alt-comedy like Judd Apatow, Dino Stamatopoulos, Janeane Garofalo, and his future-best collaborator, David Cross.

The Birth of Mr. Show

HBO

Cross and Odenkirk would team up to create their ultimate act: Mr. Show with Bob and David. Featuring several cast and crew from The Ben Stiller Show and introducing recognizable talents such as Jack Black, Tom Kenny, Karen Kilgariff, Sarah Silverman, Brian Posehn, and many more, Mr. Show was a hit among alt-comedy fans, later leading to its cult status. Mr. Show is heavily inspired by one of Odenkirk’s all-time favorites, Monty Python’s Flying Circus, particularly in timelessness, tone, and structure.

Related: Here’s How Tim and Eric Changed the Face of Comedy

Like Flying Circus, Mr. Show combines typical comedic cynicism with a surreal absurdity that ends up highlighting just how nonsensical the real world is. There’s “The Audition,” in which Cross plays an actor desperately trying to finish his monologue, only for the casting directors (Odenkirk and Stamatoupolos) to keep messing it up. The setup is banal, but Cross plays the role with such candor that it’s hard not to feel for him.

Another sketch, “Spite Marriage,” sees Odenkirk and Cross as two toxic guys whose barroom game of chicken turns into a happy, lifelong marriage. In “The Story of Everest,” a young man returns home to tell the world how he conquered Mt. Everest, only for the accomplishment to be overshadowed by a series of pratfalls. Each sketch goes in memorable, unexpected directions, and Odenkirk and Cross’s absurdist humor would resonate with just the right audiences.

The Next Generation of Comedy

Netflix

Tim Heidecker and Eric Wareheim were huge fans of Mr. Show; their out-there, surreal sensibilities are clearly inspired by the work of those earlier comedians. The two created several DVD compilations of their work and sent one, along with an itemized bill for the DVD, accompanying video, and shipping costs, to Odenkirk. Impressed, he flew the two from Pennsylvania to LA and went on to produce both Tom Goes to the Mayor and Tim and Eric Awesome Show, Great Job! for Adult Swim, which themselves garnered a cult fan base and influenced the next generation of alt-comedy.

In 2015, Mr. Show would make a brief but magnificent return to our screens as the four-episode W/ Bob & David on Netflix. Critics consistently recognized the series as a return to form, as if it had never gone off the air in the first place. “Resolutions” and “Good Cop/Bad Cop” are two favorites, but the short runtime makes it easy to binge the entire thing in a single sitting.

Odenkirk is mostly an actor and producer lately, contributing his unique voice and style to the creative works of others, but looking back on his career makes it abundantly clear just how pivotal he was in creating the comedy of today.