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Standup Comedy to Western TV Icon Journey


Best known as the gunslinging lawman of TV Westerns <em>Deadwood</em> and <em>Justified</em>, it’s hard to imagine Timothy Olyphant as anything but a master of his acting craft. However, Olyphant’s first step towards fame and fortune was actually giving a very different kind of performance.

Back in the early 1990s, long before he made his screen debut, Timothy Olyphant tried his hand as a standup comic in Boston and New York. While he ultimately took his career in a different direction, he was fairly committed to touring his standup routine for a while.

Olyphant’s best movie and TV performances might not suggest that his initial route to success involved telling jokes onstage, but that’s exactly how he got into show business. In fairness, he never lost his razor-sharp sense of comic timing, which still comes through in many of his dramatic performances.

The history of TV and cinema is littered with examples of comedic actors nailing serious dramatic roles, but Timothy Olyphant has taken things a step further. He’s made his name as a serious dramatic actor having turned his back on standup comedy early in the game.

Timothy Olyphant Is The Greatest Western TV Actor Of Modern Times

Timothy Olyphant grimacing in Deadwood

Timothy Olyphant grimacing in Deadwood

In any conversation about the best Western TV characters ever created, at least two of Olyphant’s portrayals invariably get a mention. His performances as Deadwood’s sheriff Seth Bullock and Justified U.S. marshal Raylan Givens are fundamental to the success of these characters and their shows.

Olyphant imbues both roles with the kind of depth and complexity that most actors in a genre renowned for its reliance on sheer screen presence could only dream of. Since Deadwood and Justified have ended, he’s returned to the Western genre to play Fargo’s Dick “Deafy” Wickware with aplomb, and reprised his role as Givens in Justified: City Primeval.

Timothy Olyphant as Clark in Stick

Anyone who’s seen Timothy Olyphant’s hilarious turns in Santa Clarita Diet, The Grinder, or The Office will know that he’s always had the chops for scene-stealing comedy roles. Even in Deadwood and Justified, he delivers slick one-liners with the kind of abandon only a professional comedian could carry off.

That’s because, after dropping out of college in the late 1980s, he moved to New York with the aim of becoming a professional comedian. He got his first gigs after flyering in Boston, and his best routines featured jokes about the artistic merits of pornography and making fun of MC Hammer’s most famous lyric (via Uproxx).

In the end, Olyphant couldn’t hack the relentless touring schedule of standup, and opted for acting instead, having enjoyed a drama class he’d taken at university. It proved to be a smart move, but he retained the sense of humor he’d honed on the standup circuit even after switching careers.

His Western Roles Have Made Him One Of The Best Dramatic Actors In Television History

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If we rank Timothy Olyphant’s best TV characters, Raylan Givens and Seth Bullock are way out in front as all-time greats. These characters were the first that truly demonstrated Olyphant’s dramatic acting chops. He’s played plenty of memorable comedic roles either side of these two, but he’s now more celebrated for his serious performances.

Deadwood and Justified should take a lot of the credit for reviving the TV Western on the higher plane of prestige television. But they also gave rise to one of the 21st century’s unsung acting greats, in lead star Timothy Olyphant.

Source: Uproxx

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Sarah Parker
Sarah Parker is a research analyst and content contributor with a strong interest in business strategy, organizational behavior, and social development. With a background in sociology and public policy, she focuses on exploring the intersection between research and real-world application. Sarah regularly contributes articles that bridge academic insights and practical relevance, aiming to foster critical thinking and innovation across sectors.