Timothy Olyphant's Apple TV Series Is Officially Back, And It Doubles Down On An Exciting Character Detail

Published Nov 11, 2026, 6:02 PM EST Cathal Gunning has been writing about movies, television, culture, and politics online and in print since 2017. He worked as a Senior Editor in Adbusters Media Foundation from 2018-2019 and wrote for WhatCulture in early 2020. He has been a Senior Features Writer for ScreenRant since 2020. While Timothy Olyphant was already having a massive 2026, his Apple TV show’s sophomore season has now made the actor’s character even more intriguing. When Timothy Olyphant first rose to prominence in the late ‘90s, it would have been hard to believe that the actor could become Hollywood's go-to onscreen cop alongside Mark Ruffalo in the 2020s. After all, many of his earliest major roles were on the other side of the legal divide. From playing a memorable villain in Scream 2 to a star-making role as a charismatic drug dealer in the underrated 1999 cult classic Go, Olyphant gradually emerged as a killer big screen villain in this era. However, after starring as Detective Drycoff in 2000’s Gone in 60 Seconds, Olyphant evidently felt like he had found a calling judging by the next two and a half decades of his career. Olyphant went on to portray sheriffs in Deadwood and The Crazies, a CIA agent in Snowden, a US Marshal in Fargo, and a cop in Havoc. Of course, this rundown doesn’t even mention his FX classic Justified, the six-season Neo-Western masterpiece that starred Olyphant as Deputy U.S. Marshal Raylan Givens. This gritty thriller gave Olyphant the role of a lifetime, but it also meant that, between Justified’s run and his Netflix romcom Santa Clarita Diet, viewers were deprived of seeing Olyphant in outright villainous small screen roles for a while. Luckily, Apple TV’s golf comedy Stick soon fixed this oversight in 2025. Timothy Olyphant Is An Even Bigger Villain In Stick Season 2 Justine Yeung/©Apple TV/Courtesy Everett Collection From appearing in an episode of the long-running cartoon classic The Simpsons to guest starring in American Dad, Curb Your Enthusiasm, The Office, The Mindy Project, and My Name Is Earl, it is fair to say Olyphant loves a small screen comedy role. However, Stick brought together two of the star’s best trends with a comedic villain role for the actor to sink his teeth into. Stick centers on Owen Wilson’s bitter former golf pro Pryce Cahill, who begins to turn around his mess of a life when he helps Peter Dager’s gifted golf prodigy Santi Wheeler find his feet on the professional circuit. While Stick season 1 was an attempt at a redemption arc for Pryce, he was constantly tested in his attempts to improve his outlook, most notably by Olyphant’s odious rival player, Clark Ross. Formerly Pryce’s playing partner, Ross became a smarmy, self-satisfied entrepreneur in the years since he fell out with Pryce. Although he is portrayed as a wealthy steakhouse owner and golf academy head in season 1, Ross returns in Stick season 2 to challenge Pryce to rejoin the pro tour. Since it was Ross’s nasty comments to Pryce that derailed his pro career years earlier, this challenge carries a lot of weight for Wilson’s embittered antihero. Timothy Olyphant's Year Is About To Get Bigger After Stick's Successful Return Olyphant’s villain will be a major presence in Stick season 2, giving the star another opportunity to relish a darker role. However, this is far from the star’s only major part in 2026. Olyphant has been everywhere this year, playing the title character’s imprisoned father in Apple TV’s crime thriller Lucky as well as starring in Peacock’s Elin Hilderbrand adaptation The Five-Star Weekend alongside Jennifer Garner, Regina Hall, D’Arcy Carden, and Gemma Chan, the star of the underrated British sci-fi series Humans. As if this weren’t enough, Olyphant is soon set to play James Stacy in director David Fincher’s The Further Mis-Adventures of Cliff Booth, the hotly anticipated sequel to Quentin Tarantino’s 2019 hit Once Upon a Time in Hollywood. While Leonardo DiCaprio won’t return for this follow-up, Brad Pitt, Yahya Abdul-Mateen II, Elizabeth Debicki, Scott Caan, and Carla Gugino all join Stick season 2 star Olyphant in the upcoming movie. Release Date June 4, 2025 Network Apple TV+