Timothy Olyphant is well-known for starring as lawmen and marshals on television and in movies, but he's also a successful comedic actor as well. He's best known for his roles as Raylan Givens on Justified and Seth Bullock in Deadwood, which are dramatic roles with a good amount of comedy.
Olyphant has fully shown his comedic acting skills when he starred in the comedy-horror show Santa Clarita Diet and has had entertaining guest spots in several popular shows from The Mandalorian to The Office.
The Grinder (2015–2016) - 7.1
Rob Lowe starred as an actor who played a lawyer for years on tv and decided to join his real-life lawyer brother (Fred Savage) and offer his unwanted help on cases. Timothy Olyphant guest-starred in multiple episodes of the series as a hilarious fictionalized version of himself and fellow actor frenemy to Lowe's character.
Olyphant poked fun at his career throughout his episodes including making several puns about the show he's best known for, Justified.
The Joel McHale Show with Joel McHale (2018) - 7.2
Timothy Olyphant and Drew Barrymore appeared in one episode of Joel McHale's Netflix show to promote their own Netflix series, Santa Clarita Diet.
It's a small appearance, but a fun one as the two show their comedic acting skills already established in Santa Clarita Diet as they exchange witty words with host McHale.
The Mindy Project (2012–2017) - 7.4
Timothy Olyphant appeared in one episode of The Mindy Project and briefly dated the main character, Mindy Lahiri. He played an irresponsible and tattooed skater boy who Mindy decides she should date to have some carefree fun in her life.
Their relationship falls apart pretty quickly since Mindy is a successful doctor and Olyphant's skater boy still acts like a kid. It's a hilarious episode and Olyphant portrays a character unlike any other role he's had.
The League (2009–2015) - 8.2
Timothy Olyphant guest-starred in one episode of The League, which is a series about a group of close-knit friends obsessed with fantasy football. In the episode, Olyphant portrays a sushi chef who Ruxin (Nick Kroll) doesn't trust to prepare his food because he's white and not Japanese.
It's a funny episode that again sees Olyphant portray a character he doesn't normally play as the hapless sushi chef who turns into Ruxin's enemy.
The Good Place (2016–2020) - 8.2
Timothy Olyphant appeared in one episode of The Good Place near the end of the series. The Judge (Maya Rudolph) had established that she is an obsessive fan of good television and had just started watching Justified and was a fan of the actor.
When the group needed to convince the Judge to give them more time to make an argument, Janet decides to materialize an Olyphant dressed in Raylan Givens clothing to help sway her.
Archer (2009– ) - 8.6
Timothy Olyphant voiced Lucas Troy on Archer in one episode of the series. Troy and Archer were best friends when they were training to be spies together, but Troy was accused of being a mole in the organization and defecting for a bigger paycheck.
Eventually, Troy was presumed dead, but Archer didn't believe his best friend could be gone so he finds him in a remote area having faked his death and opened a bed and breakfast. The two reconnect, but then Archer has to decide which side to take, his best friend's or his co-workers.
Curb Your Enthusiasm (2000– ) - 8.7
Timothy Olyphant guest stars on one episode of Larry David's Curb Your Enthusiasm as a mutual friend to the entire group. In the episode, Larry and his friends take a private plane to Olyphant's character's destination wedding, which of course is not an easy trip as the group begins to argue.
Larry starts to dislike Olyphant's character and complains about everything, which none of the other group agrees with since his character is similarly laid-back and nice, similar to most of the other characters he's portrayed.
Fargo (2014– ) - 8.7
Timothy Olyphant appeared in most of the latest fourth season of Fargo as U.S. Marshal Wickware, who quickly becomes an annoyance in the lives of Kansas City criminals.
He's a determined and devout character who is almost unstoppable in his pursuit of escaped criminals. Again, Olyphant portrays an engaging and likable lawman.
The Mandalorian (2019– ) - 8.7
Timothy Olyphant appeared in the first episode of season 2 of The Mandalorian as Cobb Vanth, a de facto Marshal of a small town of Tatooine who found Mandalorian armor and started protecting people in the town. Din Djarin looks for his fellow Mandalorian and finds Vanth, who has the armor but is not actually a Mandalorian.
The two make a deal when Djarin agrees to help destroy a monster that's wreaking havoc in the town in exchange for the armor. His character has already become a fan-favorite and hopefully, their paths will cross again soon.
The Office (2005–2013) - 8.9
Timothy Olyphant guest-starred on The Office for a few episodes and portrayed a rockstar salesman that the Dunder Mifflin team wanted to hire. Olyphant's character was a perfect salesman and most of the employees were hilariously in love with him when he appeared in the Scranton office.
The Office had a great cast of famous guest stars when it was on the air and Timothy Olyphant's few episodes certainly make the list.