Timothy Olyphant’s breakout role was in the acclaimed Western series,Deadwood, but six years prior to his star-making turn, he appeared in a much different HBO series,Sex and the City. While the iconic ’90s rom-com series made household names out of Sarah Jessica Parker, Kristin Davis, Kim Cattrall, and Cynthia Nixon, there were many A-listactors who guest-starred onSex and the Citybefore they were famous. Many of them played one-off love interests of Carrie, Charlotte, Samantha, or Miranda, including Olyphant.

As a whole, Olyphant has made a name for himself appearing in Western movies and TV shows. Though Seth Bullock is undoubtedly his most famous role, Olyphant appeared inJustifiedjust four years after appearing inDeadwood. The actor may look like a classic leading man, but Olyphant showed excellent anti-hero range as Deputy U.S. Marshal Raylan Givens throughoutall six seasons ofJustified. He’s also played heroes and villains alike in his film roles, and always steals any scene he’s in. This includes his small but memorableSex and the Cityrole.

Sam (Timothy Olyphant) shirtless as Carrie (Sarah Jessica Parker) begs him for coffee in Sex and the City

Timothy Olyphant Played One Of Carrie’s Love Interests In Sex And The City Season 1

Sam Was A Twenty-Something Guy Who Catches Carrie’s Attention

Timothy Olyphant’sSex and the Cityrole was way back when the show was in its infancy, in season 1, episode 4, “Valley of the Twenty-Something Guys”. In the episode,Carrie and her thirty-something friends are exploring dating younger men in their twenties, including Olyphant’s Sam. Charismatic and self-assured, Sam catches Carrie’s eye at a packed restaurant opening where he easily scores her and Miranda cocktails because he has an in with the bartender.

At this point in the series,Carrie and Big’sSex and the Cityrelationshipis in its infancy, and she’s finding herself increasingly vexed at his vague and non-committal attitude toward her. In contrast,Sam is uncomplicated and lives in the moment, so after Carrie’s attempt at a first date — or “drinks thing” — with Big goes bust, she finds a steamy palate cleanser in Sam.

Carrie (Sarah Jessica Parker) and Sam (Timothy Olyphant) caught post-makeout in a change room in Sex and the City

However,in the harsh light of the day, Carrie wakes up to all the downsides of dating a twenty-something guywhen you’re a thirty-something woman. His apartment looks like a frat house war zone, he has a roommate he never mentioned, and worst of all, there’s not a square inch of toilet paper to be had — he used the last of it as a makeshift coffee filter. Suffice it to say, Sam is never seen in the series again, but Olyphant certainly left his mark as one ofSex and the City’s most memorable guest stars.

Sex And The City Let Olyphant Show Off His Comedic Chops

He’s Mostly Known For Dramatic Roles

Between Seth Bullock and Raylan Givens, Timothy Olyphant is mostly known for his serious and gritty dramatic roles, but he’s absolutely hilarious in hisSex and the Citycameo. While he and Sarah Jessica Parker have great chemistry together as two people deep in lust for each other, it’s even better during the horror show she wakes up to. Poor 32-year-old Carrie just wants some coffee, but Sam wakes up full of pep, eager to tell Carrie about his surreal dream and completely oblivious to her discomfort.Olyphant is totally having fun hamming it upin the role.

Sex and the City(1998)

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Santa Clarita Diet(2017-2019)

Joel Hammond

This isn’t the only time Olyphant has done comedy either, and it’s something the actor clearly has a gift for.Olyphant also starred in the woefully underratedSanta Clarita Diet, a three-season Netflix comedy series about a married couple whose life becomes complicated when wife Sheila (Drew Barrymore) becomes undead and develops a taste for human flesh. Olyphant shines as the straitlaced, eager-to-please husband, Joel. Andin addition to his TV work, Olyphant has added gut-bustingly funny, unhinged mania to movieslikeThe Girl Next DoorandThe Perfect Getaway.

Olyphant Should Do Rom-Coms More Often

It’s A Genre That The Actor Hasn’t Explored Much

Out of all Carrie’s short-lived romances inSex and the City, her fling with Sam is one I treasure the most. Though it would have made no sense for Olyphant’s character to be in more than one episode, I hold out hope that he could be anEaster egg inAnd Just Like That. I’m alsoclamoring for Olyphant to appear in a rom-com because, as far back asSex and the City, he’s proven that he has charisma to burn, and Sam was just a hilarious Mr. Wrong. Imagine him as a leading man Mr. Right.

It may not be a rom-com, butSanta Clarita Dietshows that Olyphant can play softer characters just as well as antiheroes. His Joel Hammond is head-over-heels in love with his flesh-eating wife, Sheila, and that doesn’t change just because of her undead status. Whether it’sSanta Clarita Diet,Deadwood, orSex and the City, Timothy Olyphant is one of today’s most versatile working actors, and now is the perfect time to add a rom-com to his filmography.

Deadwood TV Series Poster

Sex and the City

Cast

Sex in the City follows Carrie Bradshaw, a New York writer who finds inspiration for her column from the genuine, emotional, and often humorous exploits of life in the city. Joined by best friends Miranda Hobbes, Charlotte York, and Samantha Jones, Sex and the City follows the ups and downs of the characters' romantic relationships, being single, sex, and friendship as 30-something women.

Deadwood

Deadwood is a western drama series created for HBO by David Milch. The series takes place in Deadwood, South Dakota, where corruption runs rampant in the gold-mining era as the settlement existed outside the U.S. territory expansion following the Civil War. As the town was the site of a major gold find, it continues to attract people from all walks of life - especially opportunistic criminals.

Santa Clarita Diet

Joel and Sheila Hammond live a typical life as real estate agents in Santa Clarita, California, but all that changes when Sheila becomes a zombie and starts craving human flesh. This horror comedy stars Drew Barrymore and Timothy Olyphant and lasted for a total of three seasons before being canceled in April 2019.

Santa Clarita Diet Poster