Timothy Olyphant
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50 free Timothy Olyphant trivia questions with answers — trivia quiz, new questions added Aug 2026.
Timothy Olyphant was a USC swimmer and a Vanderbilt descendant who drifted into acting by way of stand-up, a Macy's-elf monologue and a run of grinning villains in Scream 2, Go and The Girl Next Door. Then David Milch handed him a badge in Deadwood, Elmore Leonard's Raylan Givens made him the hat-wearing face of Justified, and he spent the gaps guest-starring on half the sitcoms on television. These 50 questions cover the whole career: the Honolulu birth and Modesto childhood, the 77 Sunset Strip pilot Clint Eastwood walked away from, the Fast and Furious lead he passed on, Agent 47 and the shaved head, Thomas Gabriel, Seth Bullock, Raylan Givens and the Emmy nomination, Rango, The Office and The Mindy Project, Santa Clarita Diet, James Stacy in Once Upon a Time in Hollywood, Cobb Vanth, City Primeval and Alien: Earth, plus the two years he phoned in sports reports to an LA radio show whose weatherman was David Lynch. Easy questions stick to the famous roles; the expert tier asks about Lonergan plays, Call of Duty and Practical Magic. Every answer is cited to a page we checked, with a short explanation so you learn something even when you miss. Play it solo or print it for a TV night.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In Justified's opening scene, Raylan Givens shoots a gangster across a restaurant table in which city?
Miami
Miami. He had given the man 24 hours to leave town, and although the shooting is ruled justified, it gets him sent back to the home state he had been glad to leave.
Q 02Which sheriff did Olyphant play in HBO's Deadwood?
Seth Bullock
Seth Bullock. The real Bullock came to Deadwood in 1876 to sell hardware, was made sheriff by the territory's governor a year later, and is said to have tamed the camp without killing anyone.
Q 03On which network did Justified air?
FX
FX. He had already impressed the channel in a guest role on another of its dramas, and on Justified he became a co-executive producer as well as the star.
Q 04Which novelist created Olyphant's Justified character?
Elmore Leonard
Elmore Leonard. He introduced the marshal in the 1993 novel Pronto, then liked the series so much that the show inspired his last novel, Raylan, in 2012.
Q 05In which state was Olyphant born?
Hawaii
Hawaii. He was born in Honolulu but grew up from the age of two in Modesto, California, the farm town George Lucas put on screen in American Graffiti.
Q 06Olyphant is a descendant of which famous American family?
Vanderbilt
Vanderbilt. His fourth great-grandfather Cornelius Vanderbilt started out at 16 running a ferry across New York Harbor and ended up one of the richest Americans in history.
Q 07In which sport was Olyphant a national finalist in 1986?
Swimming
Swimming. He had trained since he was six, and reaching the 200 individual medley final at the 1986 nationals won him a place on one of the country's top college teams.
Q 08Which West Coast university recruited Olyphant for his sporting talent?
USC
USC. He arrived expecting to study architecture, was told it would never fit around training, and discovered the fine arts department instead.
Q 09In which 2010 horror remake did Olyphant play a small-town sheriff caught inside a military quarantine?
The Crazies
The Crazies. His Sheriff Dutten works out that the town's water is turning neighbours into killers and shuts off the supply himself after the mayor refuses.
Q 10In which anthology crime series did Olyphant play 'Deafy', a Mormon U.S. marshal, in 2020?
Fargo
Fargo. In the fourth season, set in Kansas City in 1950, his marshal Dick 'Deafy' Wickware rides into a gang war while hunting a pair of fugitive bank robbers.
Q 11In Daisy Jones & the Six, what is Olyphant's character Rod Reyes?
The band's tour manager
The band's tour manager. It is Rod who first tells the unknown Pittsburgh group to move to Los Angeles, the advice that sets the whole story in motion.
Q 12Olyphant originated a one-man show based on which writer's essay about being a Macy's elf?
David Sedaris
David Sedaris. Olyphant was the first actor to play the elf when Joe Mantello turned the essay into a one-man play in 1996, and it has been a seasonal staple of American theatres ever since.
Q 13Which actor played saloon keeper Al Swearengen opposite Olyphant's sheriff in Deadwood?
Ian McShane
Q 21In which 2004 teen comedy did Olyphant play Kelly, a menacing adult-film producer?
The Girl Next Door
The Girl Next Door. He nearly skipped the audition, feeling he had played the type before, until his manager pointed out that hardly anyone had seen those films.
Q 22Which Stephen King adaptation featured Olyphant as one of four friends attacked by aliens?
Dreamcatcher
Dreamcatcher. He is Pete, one of four friends who gained telepathic powers as boys after rescuing another child, and whose yearly hunting trip in Maine turns into an alien invasion.
Q 23Who created Deadwood, the HBO western in which Olyphant played the town's sheriff?
David Milch
Ian McShane. His Swearengen spends the series locking horns with the sheriff, and the character was real: the historical Al Swearengen ran the Gem, the camp's most notorious brothel.
Q 14In which 1996 film did Olyphant make his feature debut?
The First Wives Club
The First Wives Club. He plays a hot young director who offers Goldie Hawn's fading star a part in his film: not the leading lady she expects, but the heroine's ageing mother.
Q 15In which 1997 horror sequel did Olyphant play a film student revealed as a killer?
Scream 2
Scream 2. He played Mickey, and later called the part a gift, because at that point he had virtually nothing on his résumé and suspects some of what was there had been made up.
Q 16Before he was famous, Olyphant played a twenty-something fling in the first season of which HBO series?
Sex and the City
Sex and the City. In the fourth episode, 'Valley of the Twenty-Something Guys', his Sam charms Carrie on a night out and looks a good deal less glamorous in the light of day.
Q 17In which 1999 cult comedy, set around Christmas, did Olyphant play a drug dealer?
Go
Go. His dealer Todd holds a customer's friend as collateral until she pays, and the film's producer was impressed enough to offer him his pick of parts in his next project.
Q 18Olyphant was replaced by Aidan Quinn in which 1998 fantasy film?
Practical Magic
Practical Magic. Variety announced him in the cast alongside Nicole Kidman as rehearsals were about to begin, yet by the time the film opened the part belonged to Quinn.
Q 19Which famous role did Olyphant turn down, later taken by Vin Diesel?
Dominic Toretto
Dominic Toretto. The studio promised to green-light the film if he signed; he passed, later joking that he assumed nobody would want to watch such a thing eight or nine times.
Q 20In which car-themed blockbuster of 2000 did Olyphant play a detective on the thieves' trail?
Gone in 60 Seconds
Gone in 60 Seconds. His Detective Drycoff spends the film a step behind a crew that has to steal 50 cars against the clock, saving a 1967 Shelby Mustang nicknamed Eleanor for last.
David Milch. He had pitched HBO a drama set in ancient Rome, and only turned it into a western about a gold-rush camp because the channel already had Rome in the works.
Q 24Which villain did Olyphant play in Live Free or Die Hard?
Thomas Gabriel
Thomas Gabriel. The cyber-terrorist stages a 'fire sale', an attack meant to shut down America's computer networks; Olyphant took the part, he admits, for purely financial reasons after Deadwood was cancelled.
Q 25Which video game assassin did Olyphant play in 2007 after Vin Diesel dropped out?
Agent 47
Agent 47. He shaved his head for the part and says he could have done without it; the film took about $100 million worldwide on reviews that were, by and large, awful.
Q 26In which 2009 thriller did Olyphant play a possible serial killer stalking holidaymakers?
A Perfect Getaway
It earned him a Toronto Film Critics Association nomination for Best Supporting Actor.
Q 27In which legal thriller did Olyphant spend a season as the heroine's morally ambiguous love interest?
Damages
Damages. He appeared in 11 episodes opposite Rose Byrne and Glenn Close in 2009, and the goodwill he built with the channel led straight to the offer of Justified.
Q 28What was Justified's working title when Olyphant was first sent the pilot script?
Lawman
Lawman. The final title comes from the opening shooting, which Raylan keeps insisting was justified because the other man pulled his gun first.
Q 29In which state is Justified set?
Kentucky
Kentucky. The show's Harlan County is real coal country, yet the pilot was filmed in Pennsylvania and nearly every later episode in California.
Q 30With which Justified character did Raylan dig coal as a teenager?
Boyd Crowder
Boyd Crowder. He was written to die in the pilot, but test audiences liked Walton Goggins so much that the producers kept him, and he became the marshal's great adversary.