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Timothy Olyphant on Justified

Looking back on the career of Timothy Olyphant, it is surprising that we did not expect his casting in Season 2 of The Mandalorian any sooner. From playing the sheriff of a morally bankrupt Wild West town in Deadwood, a U.S. Marshall who fights crime like they did in the Wild West in Justified, and the star of a 1960s Wild West-set TV show in Once Upon a Time… in Hollywood, it was only a matter of time before he got the call to star in the most Wild West-style series to be part of Star Wars canon.

However, the Hawaiian-born and Modesto-raised, 52-year-old Emmy nominee is barely at all like the cowboys he plays on screen. It is easy to see, especially from numerous interviews with his good friend Conan O’Brien, the kind of down-to-earth, affable, and quick-witted guy that Timothy Olyphant (pronounced “all-uh-fint,” in case you did not know) really is behind his often rough, reckless, and (sometimes) reprehensible characters. You could even say that the husband and father has the most in common with his Santa Clarita Diet character, excluding having a wife with a craving for human flesh and all that.

What more is there to learn about the real Timothy Olyphant before we can call ourselves true fans? Perhaps these six lesser-known facts will justify your expertise on the talented and underrated star, starting with an intriguing inside look at his family history.

Anderson Cooper on Anderson Cooper 360

Timothy Olyphant Is Related To Anderson Cooper

While he is the first of his childhood home who would grow up to lead a career in acting, looking further down Timothy Olyphant’s bloodline will reveal that show business does, indeed, run in his family. He is a third nephew of late, prolific artist and socialite Gloria Vanderbilt, who was the mother of Anderson Cooper, making Olyphant and the prominent broadcast journalist third cousins. While their primary careers do differ, Olyphant and Cooper do have more in common professionally than most may realize.

Timothy Olyphant in Meet Bill

Timothy Olyphant Became A Morning Radio Sports Reporter

In 2006, Timothy Olyphant appeared on the ESPN talk show Cold Pizza to promote the romantic comedy Catch and Release when host Jay Crawford asked him about his recently acquired “morning job,” which was delivering updates in the world of sports for musician Joe Escalante’s radio show on Indie 103.1. His two-year stint calling into the now defunct Los Angeles-based punk rock station came about when, while promoting Deadwood’s third season on Escalante’s show, he expressed interest in being a part of it and suggesting being the sports guy. If Olyphant as a sports news radio announcer sounds odd, filmmaker David Lynch was the show’s resident weatherman.

Timothy Olyphant on The Grinder

Timothy Olyphant Was Asked To Play Dom In The Fast And The Furious

In retrospect, David Lynch reporting the weather is less difficult to imagine than anyone besides Vin Diesel playing Dominic Toretto, but that’s the reality we could have had if Timothy Olyphant accepted the role. While promoting Santa Clarita Diet with co-star Drew Barrymore on Watch What Happens: Live, the actor recalled to host Andy Cohen how he thought the script for 2001’s The Fast and the Furious was “stupid” and jokingly assumed that “no one is gonna wanna see this movie eight or nine different times.” However, he might have reacted differently if the offer had come after he lost his spot on Deadwood.

Timothy Olyphant on Deadwood

Timothy Olyphant More Eagerly Accepted Movie Roles After Deadwood Was Cancelled

The news that HBO pulled the plug on its successful period piece Deadwood in the middle of its third season in 2006 was especially shocking to star Timothy Olyphant, who had purchased a house right before learning about the cancellation from creator David Milch over the phone. This informed the actor’s decision to be a little less choosy about whatever offers came his way, as he recalled in the following excerpt from a 2019 Rolling Stone interview:

What we have to thank for this is the villain in [Live Free or] Die Hard and a fucking bald head in Bulgaria shooting Hitman. That's what that phone call led to. 'How about the villain of Die Hard?' I said, 'Sure.' And they're like, 'Do you want to read the script?' I said, 'I get it. I’m in. I just bought a house. Did you not hear? They just canceled my fucking show. Yes, I’ll do it.' 'What about this video game adaptation?' 'Yes to that too. I’m in. I’ve got to make up some TV money.'

With all due respect to Hitman, which was not very critically or commercially successful, and with some genuine admiration for Live Free or Die Hard, the fourth film starring Bruce Willis as John McClane, this does help explain the state of Timothy Olyphant’s career around 2007. Of course, not only would he get to return to the world of Deadwood as Sheriff Seth Bullock for its feature-length continuation in 2019, the actor would quickly bounce back from the series’ premature end as the star of another western crime drama.

Timothy Olyphant and Walton Goggins on Justified

Timothy Olyphant Kept Real Whiskey From The Set Of Justified

In addition to receiving a Best Actor Emmy nomination and genuine respect from critics and audiences for his role as Raylan Givens on Justified, Timothy Olyphant got to take home a little extra from the FX series. While promoting the sixth and final season of the modern western hit on his buddy Conan O’Brien’s TBS talk show, Olyphant explained how Kentucky whiskey was substituted by watered down cola while filming the series and, with help from the prop department, the actor was able to keep the poured out remains of the real product. To prove it, he brought a mason jar full of the stuff to share a toast with O’Brien and Andy Richter.

Drew Barrymore and Timothy Olyphant on Santa Clarita Diet

Timothy Olyphant And Drew Barrymore Helped A Santa Clarita Diet Fan Propose To His Girlfriend

As a small screen follow-up to Justified, Timothy Olyphant took the role of a California real estate agent struggling to provide his undead wife (Drew Barrymore) with a feast of human remains on Santa Clarita Diet, a short-lived, but much-loved, Netflix original. In 2017, the actor and his romantic lead would spread the romance by helping a man named Conor make his marriage proposal to girlfriend Kamela - a fan of the dark comedy - an even grander surprise. A heartwarming video of the occasion shared on Netflix’s Twitter sees the couple watching a video of Olyphant and Barrymore before Conor unexpectedly appears on the TV to set the real him up to pop the question.

What do you think? Has this closer analysis of Timothy Olyphant convinced you to rewatch his best work all over again, or do you feel that you will never be able to take him seriously in an action role anymore? Let us know in the comments and be sure to check back for additional information and updates on the star of The Mandalorian’s second season, as well as even more inside looks into the lives of your favorite celebrities, here on CinemaBlend.

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