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Olyphant was born in Honolulu, Hawaii and moved to Modesto, California, a rural town east of San Francisco, at the age of 2, where he was raised. His father worked for a winery. Olyphant began competitive swimming at age 6, and started training seriously in the seventh grade. He was a finalist at the USA Swimming Short Course National Championships in 1986 in the 200 Individual Medley. He graduated from Modesto's Fred C. Beyer High School that year.
Olyphant continued swimming at the University of Southern California in Los Angeles, where he studied fine art. He took a beginning acting class as an elective at UC Irvine, in order to fulfill the final credits he needed to graduate from USC. Olyphant then decided to move to New York City to study acting, rather than pursue a master's degree in fine arts. He took acting classes with William Esper at William Esper Studio for two years, and then started looking for acting work.
Olyphant began acting off-Broadway, making his professional debut in 1995 in the Playwrights Horizons' production of The Monogamist as Tim Hapgood. He received the Theatre World Award for Outstanding Debut Performance for his performance. He subsequently appeared in the one-man play The SantaLand Diaries in 1996, written by David Sedaris, adapted and directed by Joe Mantello, and in Plunge.
Olyphant returned to Los Angeles and found work in television. He landed his first TV role in a pilot for a remake of the series 77 Sunset Strip in 1995, produced by Clint Eastwood. He was cast in the pilot of Mr. & Mrs. Smith (1996), a short-lived CBS spy series, as Scooby, Mr. Smith's (Scott Bakula's) assistant. Olyphant appeared in 3 episodes of the acclaimed police drama High Incident and in the Hallmark Channel TV film Ellen Foster in 1997. A role in the HBO movie When Trumpets Fade was next in 1998, a dramatization of the 1944 Battle of Hürtgen Forest, followed by a guest starring role in the Sex and the City episode "Valley of the Twenty Something Guys", as one of Carrie Bradshaw's boyfriends.
Olyphant made his feature film debut with a small part in The First Wives Club (1996). He appeared briefly in A Life Less Ordinary (1997), starring Ewan McGregor, but gained notice starring in the horror film Scream 2 (1997), as a cynical film student, Mickey. He portrayed the drug dealer Todd Gaines in Go (1999), directed by Doug Liman, a comedy-drama with Katie Holmes, Scott Wolf and Sarah Polley in the cast, and a script by first time screenwriter John August. He followed the role up with parts in Advice from a Caterpillar (1999), No Vacancy (1999), The Broken Hearts Club: A Romantic Comedy (2000) and Gone in 60 Seconds (2000).
Olyphant played the lead role of Sheriff Seth Bullock on HBO's Deadwood from March 2004 until the series' end. Olyphant considered it to be one of his first leading roles as a "complicated" and "complex" character. Prior to that he had roles in Rock Star (2001) and Dreamcatcher (2003). He played a porn film producer in The Girl Next Door in 2004 alongside Emile Hirsch and Elisha Cuthbert.
In January 2007, Olyphant appeared in the comedy Catch and Release, playing the love interest of Jennifer Garner's character; Olyphant was cast in the role over several other known actors, including Matthew Fox. Olyphant had studied acting alongside Jennifer Garner when he moved to New York. He next appeared in Live Free or Die Hard, as the villain, a cyber-terrorist and in Hitman, as the title character. Olyphant shaved his head for his role in Hitman. His 2008 roles included Stop-Loss, about the Iraq War, playing a Lieutenant Colonel, Meet Bill, a comedy co-starring Aaron Eckhart and Jessica Alba, and a voice-acting role in Turok (2008) as Cowboy.
In 2009, he starred with Steve Zahn and Milla Jovovich in the thriller A Perfect Getaway as an Iraq war veteran and possible serial killer of honeymooners on the Hawaii islands. In late November 2008, it was announced that he had officially signed on for the lead role of the town sheriff in the 2010 film The Crazies.
In the spring of 2010, Olyphant began portraying the lead role of Raylan Givens in the FX series Justified. His character is a 21st century U.S. Marshal who, for his questionable tactics, is banished to the part of Kentucky in which he was born and raised. Givens wears a Stetson hat and behaves like an Old West sheriff. The show is based on a character created by Elmore Leonard in the novels Pronto and Riding the Rap, and the short story "Fire in the Hole". The pilot episode was an adaptation of the latter. Olyphant plays a paper salesman in fall 2010 season 7 of NBC Television's hit comedy, The Office.
|1996||Mr. & Mrs. Smith||Scooby||Pilot guest star|
|1997–1998||High Incident||Brett Farraday||Recurring role, 3 Episodes|
|1998||Sex and the City||Sam||Guest star, 1 Episode|
|2002||Night Visions||Eli||Guest star, 1 Episode|
|2004–2006||Deadwood||Sheriff Seth Bullock||Ended|
|2006||My Name Is Earl||Billy Reed||Guest star, 1 Episode|
|2009–2010||Damages||Wes Krulik||Regular season 2 only|
|2009||Samantha Who?||Winston Funk||Recurring role, 2 Episodes|
|2010||The Bonnie Hunt Show||himself||Talk show|
|2010–present||Justified||Raylan Givens||Series regular|
|2010||The Office||Danny Cordray||Guest star|
|1996||The First Wives Club||Brett Artounian|
|1997||A Life Less Ordinary||Hiker|
|Scream 2||Mickey Altieri|
|1998||1999 (Girls and Boys)||Hooks|
|When Trumpets Fade||Lt. Terrence Lukas|
|Advice from a Caterpillar||Brat|
|2000||Gone in 60 Seconds||Det. Drycoff|
|The Broken Hearts Club: A Romantic Comedy||Dennis|
|2001||Head Over Heels||Michael|
|Auggie Rose||Roy Mason|
|Rock Star||Rob Malcolm - Guitarist, Blood Pollution|
|2003||The Safety of Objects||Randy|
|A Man Apart||Hollywood Jack|
|2004||The Girl Next Door||Kelly|
|2007||Catch and Release||Fritz|
|Live Free or Die Hard||Thomas Gabriel||(also known as Die Hard 4.0)|
|2008||Stop-Loss||Lt. Col. Boot Miller|
|2009||A Perfect Getaway||Nick||Nominated — Toronto Film Critics Association Award for Best Supporting Actor|
|2010||The Crazies||David Dutten|
|Hitman 2||Agent 47||being scripted|
|2011||I Am Number Four||Henri||In production|
|Rango||The Spirit of the West||voice only|