Timothy Olyphantis likely best known for his various television roles, but given the high-quality - and oftentimes cinematic - nature of TV in the last couple of decades, that’s nothing to be ashamed of. Olyphant is most likely to be recognized for playingSheriff Seth Bullockin the acclaimed historical drama/Western seriesDeadwood, as well as playing a more modern-day Marshal inJustified.Olyphant excels at playing tough guys and/or anti-heroes, but has also been a compelling villainon more than a few occasions.
These various types of roles can be found throughout his filmography, which is one body of work that shows Olyphant can excel outside television, too. The following movies are some of his most critically acclaimed, being ranked below by their Rotten Tomatoes scores. There are plenty of other noteworthy films (and TV shows, of course) that he’s been in, but the following titles can nevertheless be counted among Timothy Olyphant’s best work.
10’National Champions' (2021)
Rotten Tomatoes Rating: 66%
Everyone lovesa good sports movie, even if the genre is one that often relies on well-worn storytelling devices, perhaps more so than most other genres. The good ones tend to bring something new to the table, or are well-made/well-acted enough that viewers will be willing to accept some level of clichés being present.National Championsultimately succeeds because it’s more of a drama than a sports movie, centering on what happens when the players of a college football team go on strike.
The strike is announced just hours before an important game, which naturally makes things feel high-stakes and intense. The central premise feels extra relevant in the wake of allthe entertainment industry-related strikes of 2023, and even ifNational Championscan’t quite escape feeling like an adaptation of a stage play, the cast members all make it work and keep things interesting, with Olyphant’s supporting role inevitably supporting the lead performances from the likes ofStephan JamesandJ. K. Simmons.
Watch on Netflix
9’The Crazies’ (2010)
Rotten Tomatoes Rating: 71%
The Crazieswas a 1973 movie directed byGeorge A. Romerothat’s not often held up as one of the filmmaker’s best, though it’s solid enough. There are arguably too many horror remakes out there, but the idea of redoing one that wasn’t an absolute classic is a little easier to digest. Enter 2010’sThe Crazies, which takes the same premise found in the 1973 film of the same name and gives everything a more modern edge.
Timothy Olyphant plays a sheriff here, one year before he’d play an Old West equivalent inDeadwoodand several years before he played a Marshal inJustified.The Craziesis about his character and various other members of a small town dealing with a biological agent that has disturbing effects on people who come into contact with it, turning them violent and without reason. Perhaps you could do better, as faras intense/gruesome horror movies go, butyou could also do much, much worse than this remake ofThe Crazies.
The Crazies
Rent on Apple TV
8’High Life' (2009)
Rotten Tomatoes Rating: 80%
Not to be confused with thehaunting and unusual sci-fi movieof the same name from 2018, 2009’sHigh Lifeis entirely different, given it’s a blend of comedy, thriller, and crime genres. It’s gritty and overall small-scale, being one of the less well-known Timothy Olyphant movies on Rotten Tomatoes, on the basis of its small number of reviews on the site. Still, it currently has one negative review and four positive ones, which inevitably lead to an 80% approval rating.
The main premise revolves around the disastrous planning of a seemingly simple heist, with Olyphant’s character proposing that he and a group of others attempt to steal an ATM.There might not be too many surprises to be found withinHigh Life, but heist movies can be inherently fun and satisfying, just like how traditional sports movies are, so fans of that crime subgenre wanting to seek out something lesser-known might find value in this film.
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7’Scream 2' (1997)
Rotten Tomatoes Rating: 82%
The originalScreamwas a very well-received slasher movie that also managed to poke fun at slasher movies through witty meta-commentary. Following up such a film with a worthy sequel just one year later couldn’t have been easy, butWes Cravenapproached it in a way that allowed him to provide commentary on the nature of horror sequels.It’s perhaps an expected approach, in hindsight, but it works very well, ensuringScream 2will please most people who liked the first.
Sydney Prescott finds herself in college two years on from the events of the first film, withScream 2featuring her and other survivors from the original dealing with a new Ghostface killer who seems to be a copycat of the first. Timothy Olyphant plays Mickey Altieri, one of many people who could well be the killer under the mask, and he gives a solid performance here alongside series regulars likeNeve Campbell,Courteney Cox, andDavid Arquette.
6’Live Free or Die Hard' (2007)
Few people would callLive Free or Die Hardthe best of theDie Hardfilm series, but it would also be difficult to argue it was the worst. It was thefirstDie Hardmoviein more than a decade, with the gap in release allowing John McClane to age considerably and find himself even more isolated, in many ways, thanks to the technological advances of the 2000s.Live Free or Die Hardcatapults the series into the 21st century, and there’s a thrill in seeing an old-school police officer deal with newfound threats.
Timothy Olyphant’s character is behind such threats and the film’s overall conflict, with him hamming it up wonderfully as the villainous Thomas Gabriel. Gabriel’s a cyber-terrorist who wants to bring down the U.S. largely through various devastating hacks, leading McClane (Bruce Willis) to team up with a young hacker (Justin Long) to put a stop to it all.Live Free or Die Hardgets silly and perhaps too over-the-top in places, but it’s certainly entertaining, and Olyphant’s villainous turn is pretty great.
Live Free or Die Hard
5’Once Upon a Time in Hollywood' (2019)
Rotten Tomatoes Rating: 85%
Quentin Tarantino’s supposedly penultimate film,Once Upon a Time in Hollywood, has an absolutely huge cast, with numerous characters showing up in this largely funny (and occasionally violent) movie about Hollywood in the late 1960s. A struggling actor played byLeonardo DiCaprioand his loyal stuntman/friend (Brad Pitt) are generally focused on, but the rest of the cast includes big names likeMargot Robbie,Margaret Qualley,Al Pacino,Bruce Dern, and Timothy Olyphant, to name just a few.
Once Upon a Time in Hollywoodblends real-life figures with fictional characters to striking effect, with Olyphant playing someone based on a real-life person:James Stacy. DiCaprio’s (fictional) character gets cast inLancer, which was a real-life show that actually starred Stacy and aired between 1968 and 1970. It’s one of many ways that Tarantino has referenced older media throughout his filmography, with some real-life history utilized well here to tell a largely fictional story.
Once Upon a Time in Hollywood
Watch on Starz
4’Rango' (2011)
Rotten Tomatoes Rating: 88%
As far as animated (and at least partly kid-friendly) movies go,Rangohas to be one of the strangest ones in recent memory. It’sa unique take on the Western genrethat serves as a homage to classic Western tropes while utilizing unusual animation and a style that feels distinctly its own. It’s about a pet chameleon who gets lost in the desert before finding himself suddenly becoming the sheriff of a town populated by other animals.
Like all the other cast members ofRango, Timothy Olyphant is featured here in a voice role, playing a character known only as The Spirit of the West. Essentially, this figure isClint Eastwood’s character from thefilms inThe Man with No Nametrilogy, with the likeness being exactly the same as how a 21st-century Eastwood would look if he reprised the role.The character serves as one of many fun homages inRango, and though Olyphant’s voice-work here is brief, it is memorable.
Watch on Paramount+
3’Missing Link' (2019)
Another well-regarded animated movie Timothy Olyphant has a voice role in,Missing Linkwas a critically acclaimed film from Laika, albeit not one that was financially successful. Its plot revolves around an adventurous investigator who wants to find something that will surprise the scientific community, so he sets out to find proof of a strange/mystical creature that no one else seems willing to believe in the existence of.
Missing Linkhas the creative character design and distinctive stop-motion animation you’d expect from Laika, and even if it’s not quite as good as sayCoralineorKubo and the Two Strings, it still gets the job done.Missing Linkmay have gotten lost among the sea of other great movies released during 2019, however, making it one of the more underrated films Timothy Olyphant has appeared in, in some capacity.
Missing Link
2’Go' (1999)
Rotten Tomatoes Rating: 91%
Gois something of a cult classic and simultaneously quirky andmildly anxiety-inducing comedy.It’s also hard to describe, beyond saying that it might scratch the same itch asPulp Fiction, given the way it makes several storylines collide in unexpected ways, skillfully balancing numerous characters and their respective plot threads throughout in unpredictable and thrilling ways throughout its entire runtime.
Timothy Olyphant plays a drug dealer who becomes involved with several other characters and gets wronged by them, leading to a chain of events better experienced through the film than trying to understand through mere words. OnceGogets going (andGogets going pretty quick), it - fittingly enough - never really stops until the end credits begin rolling, making it a fun trip worth taking for anyone who’s yet to come across this underrated late-1990s flick.
1’Deadwood: The Movie' (2019)
Rotten Tomatoes Rating: 98%
Between 2004 and 2006,Deadwoodran for a total of three acclaimed seasons on HBO, but didn’t have the viewership needed for a fourth season. Regrettably, season 3 ended with many things unresolved, so for more than a decade, fans ofDeadwoodhad to accept the show was seemingly dead in the water, and wouldn’t be concluded. Thankfully, come 2019,Deadwood: The Moviewas made, and it raced through the sorts of events that could’ve transpired had the show gotten a season 4.
That being said, it has something of a time jump and takes away certain degrees of historical accuracy to get to a logical and fitting ending, butit does these things well and the conclusion is nevertheless very satisfying, makingDeadwood: The Moviean all-time great TV movie. It’s fantastic to see so many of the characters again one last time, most notably Timothy Olyphant’s Seth Bullock andIan McShane’sAl Swearengen, once again scheming, swearing, and surviving in one truly tough and unique Old West town.
Deadwood: The Movie
As the residents of Deadwood gather to commemorate Dakota’s statehood in 1889, saloon owner Al Swearengen and Marshal Seth Bullock clash with Senator George Hearst.
