Timothy Olyphant’s Top Five Lawman Roles (And Five Semi-Forgotten Olyphant Roles Worth Revisiting)

FX’s Justified: City Primeval is nearly upon us. How long have we waited for Raylan Givens to swagger back into our hearts and vanquish some bad guys as everyone’s favorite extralegal lawman So many days that I cannot bear to count them, and I can only hope that much ice cream is involved.

We recently discussed one Justified episode, “Long In The Tooth,” that makes an ideal essential rewatch before City Primeval. That particular episode showcased Raylan’s legendary status and also served as a reminder of how the Marshall Out Of Water rolls around in the world. He should also have a swell time hunting bad guys in Motor City, where his hat and boots will again be observable outside the hollers of Kentucky. The revival is based on Elmore Leonard’s City Primeval: High Noon in Detroit novel.

A few thoughts before we begin:

First, there’s never a bad time to circle back to Olyphant’s many onscreen rodeos as a lawman. He’s certainly doing nothing to deter his reputation as a charismatic wearer of badges. And he is undeniably well-suited to these swaggering roles. He can’t stop gripping that gun in the holster while strutting through America and the galaxy at large. Sure, there’s the occasional not-so-great entry — like the Jerry Bruckheimer-produced Gone in Sixty Seconds (2000), in which Olyphant was cursed with a completely generic cop character. We shall disregard that one and focus on his better lawman joints.

Second, this is also as fine a reason as any to circle back to some non-lawman Olyphant roles, which are necessarily less celebrated, but don’t let that deter you. Don’t expect a lot of prestige from these projects, either, because we are revisiting them for fun and to distract ourselves with variety before he reprises the Raylan role (and it’s about damn time).

With that said, I reckon that we should dive into both categories.

Top 5 Olyphant Lawmen Roles

5. The Crazies (2010)

Overture Films

This horror remake accomplished much more, thematically, than the original George Romero flick while also diving deep into the genre in such an intelligent way that the results were, well, a bit much. Yes, maybe this was too cerebral to be mega-successful as a genre picture (although it did well enough financially), and although this isn’t technically a zombie film, a lot of the motifs that run through those movies remain the same. Olyphant’s small-town sheriff finds himself navigating the early stages of an outbreak that turns people into irrational, unstoppable killers, and sh*t gets real with the military as martial law descends. Granted, it’s a frightening watch, but it bypasses the usual horror tropes, and we get to see him in a serious genre take many years before he went on to star in a comedic zombie series on Netflix.

This project also arrived at an interesting point in his career: a few years after Deadwood ended as an HBO TV series but right before Justified launched on FX. Any Olyphant-lawman completist should put this film on their list, but it’s not as wonderful as his other badge-filled turns for a few reasons: (1) This is not the typical Olyphant lawman who’s confidently equipped to deal with every situation, so he’s not as satisfying to witness if you’re looking for his usual mythical bent; (2) He does not wear a hat here, and I’m not sorry to say that, yes, this makes a difference.

4. Fargo (2020)

FX

This is where things get tricky, fast, because it feels somewhat criminal to rank five wonderful Olyphant performances that are all worthy of appreciation. How lucky are we, really, to have this guy embracing various incarnations of the way that he knows people love to see him most He’s a charming rascal, and he knows it. Let’s be honest, I’d even watch him don sheriff-y attire and simply make oatmeal in a slow cooker (something that he actually does in real life, although with hat status unknown) for a full season. There’s a nice suggestion for a streaming service to have for free. You are welcome.

With that said, Olyphant’s Fargo appearance didn’t reel me in quite as much as I hoped that it would. I do love where Deafy got his nickname and the whole kicking-in-the-door move and the endearing carrot-stick offering, but this recurring role doesn’t allow the Olyphant quality to shine. He’s part of an ensemble of stellar actors playing kooky roles with weird-ass names, and against that jumbled backdrop, his Stetson-wearing presence doesn’t resonate with this actor’s usual gravity. To me, Fargo Season 4 is where the understated performances — like that of Chris Rock as a crime boss — are the ones that stand out. Having Olyphant around is a fine bonus, of course.

3. The Mandalorian (2020)

Disney+

Now we’re cooking. What an absolute treat “The Marshal” episode turned out to be because it gave us Space Raylan. Will we see Cobb Vanth again It doesn’t seem likely, but we still got to witness Olyphant nerding out and looking cool at the same time in a Star Wars gig. Not even that restrictive armor could keep his personality and sardonic wit from shining through. And he did so in a role that tweaked Star Wars canon and helped to put Boba Fett back in the equation. Who would have thought that was possible Furthermore, Jon Favreau knew who to call when he needed a Marshal-type.

Sure, Cobb is a bit of an a-hole by Star Wars standards, but so was Han Solo, and both characters remain likable. And it was a blast to watch Olyphant do his part while defeating a Krayt Dragon in a truly thrilling action scene that felt Dune-esque (for the Sarlaac-turned-sandworm factor). For a moment, I even forgot all about Pedro Pascal over there with all that Mando armor. No wonder they haven’t brought Cobb back into the fold. His powerful screen presence could even make Baby Yoda cease to matter.

2. Deadwood (2004-2006 and 2019)

HBO

C*cksuckers, unite for this one. David Milch’s masterfully profane HBO western still holds up, throughout the three TV seasons (that managed to include a fine episode about… kidney stones yes) and one reunion movie full of Shakespearean dialogue and catching up with beloved figures. It’s a testament to Olyphant’s own indispensable performance (and his confidence in the role) that he was sure glad that he wasn’t the “a-hole” to turn down a return to the magic. So, we got a revisiting of the breakout part that make him well-known for wearing a hat on the wild frontier.

From the first-season episode of Seth Bullock falling to his knees while witnessing the death of Wild Bill Hickok to Bullock’s balance of contempt-respect for his frenemy, Al Swearengen, Olyphant excelled at the upholding of honor and the settling of scores. The particular gathering of ensemble personalities here, as well, did not distract from Bullock as the central beacon of the show. As Deadwood’s appointed sheriff (who thought he’d left those days behind), Bullock frequently seethed with thinly-cloaked rage after picking up the badge again. Yet Olyphant almost seems addicted to law enforcement roles, and even in 2023, he’s still enjoying taking those rides.

1. Justified (2010-2015, 2023, Eternity)

FX

Raylan Givens: the role that Timothy Olyphant was born to play. Elmore Leonard, who created the character, raved about how the show’s spin on his stories (and the leading man) blew him away. That Stetson hat, too, got tweaked as an Olyphant entry, upgraded from a “Dallas Businessman’s Special” in Leonard’s prose. And the headgear of the TV show turned out to be instrumental: you could always tell when Raylan went undercover because he’d go hatless. It was funny and fitting and fed into the mythical character who left a corrupt dentist (in the aforementioned “Long In The Tooth” episode) gasping to see his hero-nemesis coming to arrest him.

Olyphant infused Raylan with all the swagger that was fit to bloody the nose of Appalachia. It’s telling, too, how Raylan’s extralegal ways (and fried-chicken-temptation antics) managed to age well, even in a time when many are circling back to point fingers at cop shows. Yet Raylan never wielded his power against anyone who didn’t have it coming. Basically, he took down Nazis and those who refused to pick on people their own size. And even though he felt compelled to honor his dynamic with Boyd Crowder by paying the guy an in-person visit in the series finale, Raylan’s moral code never strayed from what was inherently good. Don’t tell him that, though. Like Olyphant, Raylan’s chaos-filled manner of self-deprecation remains the stuff of legends.

Five More, Semi-Forgotten Olyphant Roles Worth Revisiting

(In no particular order)

Santa Clarita Diet (2017-2019)

Netflix’s unfortunate habit of canceling ridiculously good series after three seasons has never been better illustrated than with this glorious little zombie sitcom co-starring Drew Barrymore. The comedic timing of this duo could not have been more delightful, and I lived for those moments when Joel McHale showed up as a bitchy realtor and Nathan Fillion’s disembodied head waxed rhapsodic in the basement. This was just an all-around fun little kooky show, and the fact that it got axed on a cliffhanger (we were deprived of flesh-eating Olyphant, y’all) makes this one hurt even more.

Olyphant’s reaction seemed fitting, too. In a statement, he insisted, “I loved working on this show. I’m going to continue coming in and doing scenes. If they don’t want to film it, that’s up to them.” Let’s hope that he decided to take Mr. Ball Legs home and keep that dream alive. If we can see Deadwood and Justified revivals, after all, anything is possible. Get on it, Netflix.

Go (1999)

Sony Pictures Releasing

Villainous Olyphant is not the most uncommon species. You can also see him visit the dark side in Scream 2 and Live Free And Die Hard, although I don’t find those to be the most riveting examples of his bad-boy incarnation. In Go, however, we get to see a darker Olyphant variant that was, to a degree, also spotted in The Girl Next Door, but that particular film skeeves me out because I don’t appreciate the “Perv Raylan” vibe. Whereas Go gives us a scuzzed-out Olyphant wielding sideburns and a Santa hat (always with the hats, man) that run counter to his initially intimidating vibes as a drug dealer.

Looking back, it’s a performance that perfectly mirrors his audition story (as told to GQ) of pretending that he’d never read the lines or cared about the role, when “I had fully prepared for that, and pretended like I hadn’t,” he says. He added, “I hope young actors starting out are paying attention. It’s all fair. Work really f*cking hard, and then act like you didn’t.” Now for a real bonus: go rewatch that diner scene between Olyphant and Katie Holmes and the goon-filled aftermath to remember how underrated this film remains to this day. My god, what an oddly charming discussion about The Family Circus.

A Perfect Getaway (2009)

Universal Pictures

This is a total B-movie, so place your expectations accordingly. We do, however, not only get Olyphant in a terrible hat (which he still pulls off) but also as one-half of three couples who drop red herrings like mad in Hawaii while rumors of tourist-killers circulate. One of these couples is probably out to murder everyone, and at one point, we receive a sinister Olyphant chuckle that is worth the price of admission. I’ve given that chuckle and sneer too much thought over the years, mostly because it has layers that this movie frankly doesn’t deserve, but you can never accuse Olyphant of not rising beyond the occasion, even if it feels like he just sauntered in like it’s no big thing. Also on the table: Steve Zahn and Milla Jovovich as one of the oddest couples that you’ll ever witness. The big reveal at the end is astoundingly insulting, but the ride is worth it for this atypical Olyphant flick.

Catch And Release (2006)

Sony Pictures

Speaking of curiosities, here’s Olyphant in rarified form as a straightforward romcom hero. Granted, this film is super predictable, as many romcoms are, and you can see from a galaxy away that Jennifer Garner’s grieving character, Gray, will fall for her fiancée’s buddy, Olyphant’s Fritz. As well, Kevin Smith once did an interview (which I can no longer find since it was so many years ago) in which he discussed having a not-so-great experience on the set of this film as an actor. He and Olyphant weren’t exactly pals on the set, if I recall correctly (but Smith sure did change his tune after he saw Space Raylan), yet a certain kissing scene and the sight of Olyphant playing fetch with a dog could soften even the most aromantic person’s heart.

Sex And The City (1998)

HBO

It’s Olyphant at his most revolting (you have no idea how much it pained me to type those words) and as the total opposite of a romcom king. He guest-starred in a fourth-season episode, “Valley of the Twenty-Something Guys,” as a fleeting lust interest of Carrie Bradshaw. And sure, he looked good at night and during the morning hours, but the harsh glow of daylight was too much for Carrie, given that Olydude lived in absolute sloth and used the last of the toilet paper as a coffee filter. The “worth it” part, though, was Olydude rambling about a weird dream, in which he had “hands… big hands!”

I’m so happy to have Justified: City Primeval as an upcoming palate cleanser.

FX’s ‘Justified: City Primeval’ will debut on July 18.