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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 01Which Deputy U.S. Marshal did Olyphant play for six seasons on FX?
Raylan Givens
Many critics call it the defining role of his career.
Q 02Which sheriff did Olyphant play in HBO's Deadwood?
Seth Bullock
He reprised the role in Deadwood: The Movie in 2019.
Q 03On which network did Justified air?
FX
FX president John Landgraf sent him the pilot script, then titled Lawman, after Damages.
Q 04Which novelist created Olyphant's Justified character?
Elmore Leonard
Leonard's final novel, Raylan, was inspired by the TV show.
Q 05In which state was Olyphant born?
Hawaii
He was born in Honolulu and moved to Modesto, California, at age two.
Q 06Olyphant is a descendant of which famous American family?
Vanderbilt
Cornelius Vanderbilt was his paternal fourth great-grandfather.
Q 07In which sport was Olyphant a national finalist in 1986?
Swimming
He reached the finals of the 200m individual medley and was recruited by USC.
Q 08Which university recruited Olyphant as a swimmer?
USC
Coach Peter Daland brought him in; he hoped to study architecture but was told it would clash with training.
Q 09How much later did Olyphant finish the degree he left one elective short of?
30 years
He took an online course during the COVID-19 pandemic to complete it.
Q 10What was Olyphant doing for a living before he moved to New York to try acting?
Coaching swimming
He also dabbled in stand-up comedy for about six months.
Q 11For which 1995 off-Broadway play did Olyphant win a Theatre World Award?
The Monogamist
It was his professional stage debut, at Playwrights Horizons.
Q 12Olyphant originated a one-man show based on which writer's essay about being a Macy's elf?
David Sedaris
The SantaLand Diaries premiered at the Atlantic Theater Company in 1996.
Q 13Which producer quit Olyphant's first paid job, a 77 Sunset Strip pilot, before filming?
Clint Eastwood
Olyphant never got to meet him.
In which 1996 film did Olyphant make his feature debut?
Q 21In the 2004 comedy The Girl Next Door, what was Olyphant's character Kelly's profession?
Porn film producer
He almost skipped the audition, thinking the part too like roles nobody had seen.
Q 22Which Stephen King adaptation featured Olyphant as one of four friends attacked by aliens?
Dreamcatcher
A Variety critic said only he and Jason Lee found the right tongue-in-cheek tone, and they died first.
Q 23Who created Deadwood and praised Olyphant's "thoughts too deep for words" quality?
David Milch
Olyphant calls Milch one of the greatest storytellers he has ever been around.
The First Wives Club
He played an eager young director who tries to cast Goldie Hawn as an elderly mother.
Q 15In which 1997 horror sequel did Olyphant play a film student revealed as a killer?
Scream 2
He later called the role a gift, since he had virtually nothing on his résumé.
Q 16On which HBO series did Olyphant play a love interest for Carrie Bradshaw in 1998?
Sex and the City
Sarah Jessica Parker called the episode her favourite of the whole series.
Q 17In which 1999 cult comedy did Olyphant play a drug dealer to good notices?
Go
Its producer Mickey Liddell then offered him any part in The Broken Hearts Club.
Q 18Olyphant was replaced by Aidan Quinn in which 1998 fantasy film?
Practical Magic
He had been set to star opposite Sandra Bullock and Nicole Kidman.
Q 19Which famous role did Olyphant turn down, later taken by Vin Diesel?
Dominic Toretto
The studio said it would greenlight the film if he took the part; he thought it would bomb.
Q 20In which 2000 action film did Olyphant joke about playing "second fiddle to a car"?
Gone in 60 Seconds
A Washington Post critic said his detective recalled a young Bill Paxton.
Q 24Which villain did Olyphant play in Live Free or Die Hard?
Thomas Gabriel
Both he and Bruce Willis felt the cyber-terrorist was underwritten and built him up together.
Q 25Which video game assassin did Olyphant play in 2007 after Vin Diesel dropped out?
Agent 47
He reluctantly shaved his head; the film made over $100 million despite bad reviews.
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 FX legal thriller did Olyphant play a love interest for Rose Byrne?
Damages
Byrne called him her favourite guest star; FX's president then sent him the Justified pilot.
Q 28What was Justified's working title when FX sent Olyphant the pilot script?
Lawman
He had just impressed FX president John Landgraf on Damages.
Q 29In which state is Justified set?
Kentucky
Raylan is reassigned home to Harlan County after a questionable shooting in Miami.
Q 30With which Justified character did Raylan dig coal as a teenager?
Boyd Crowder
Walton Goggins played Boyd, the outlaw who became the show's co-lead.