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twobossydames · Aug 25, 2026

What’s Your Timothy Olyphant Character Type?

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Sophie Brookover, Two Bossy Dames · twobossydames

So you, like untold fafillions of others, have gulped down all eight magic hour-suffused episodes of The Five-Star Weekend on Peacock. If so, you may well be left with a Nantucket-sized, Timothy Olyphant-shaped hole in your viewing schedule, and if that’s the case, congratulations, friend, you are in the right place.

I’m rooting for these crazy kids

Olyphant’s career is long enough and just varied enough to offer several paths to future viewing selections. As I rummage through the ol’ memory boxes, I think the best avenues to start with are: Wife Guy, Charming Roguish Lawman, and Full-On Himbo.

Aw. Look at them!

For the ultimate flourishing of Tim’s current Wife Guy incarnation, we’ll have to wait til the next season of Five-Star Weekend, but to tide us over, we have the glories of his performance as Joel in Santa Clarita Diet. It’s honestly kind of astonishing that Netflix was able to contain and channel the combined nuclear-level charm of Olyphant and Drew Barrymore playing husband and wife for a full three seasons. I’m very annoyed that there’s only three seasons of Santa Clarita Diet, but I still manage to be grateful that we got so many episodes of the funniest zombie horror-sitcom (with a bit of staying one step ahead of the law/conspiracy thriller) imaginable. Mild-mannered realtors Sheila and Joel Hammond find their lives thrown into chaos when Sheila undergoes an all-too-common transformation in her 40s. No, it’s not perimenopause! How dare you suggest such a pedestrian thing? No, she becomes a zombie. Obviously.

Poor Joel is at first dumbfounded, then 100% supportive, because he is a good and loving husband who appreciates Sheila in all her many-faceted, slightly unhinged glory. Extra points for how playing Joel gives Olyphant the chance to put his considerable comedic chops to good use. I’m also very fond of how prescient the casting director was, introducing the world to the talents of Liv Hewson, who plays the teenaged Van Palmer in Yellowjackets, as their daughter Abby, and Skyler Gisondo as their neighbor and trusted confidant, Eric.

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Charming, Roguish Lawman is probably Olyphant’s most well-established mode, and if this is your favorite tipple of Tim, you’ve got a couple of flavors to choose from. First is the highly strung jaw clenching of Deadwood’s Sheriff Seth Bullock (as I re-appreciated just a month or so ago).

Costume designer Janie Bryant knew what she was doing from jump.

Do you like when a fictional man is so morally upright that he’d marry the wife of his beloved late brother to ensure that she and her son remain under what protection he can offer as a successful businessman and interpreter of the law? And yet is so undone by his own impetuousness and horniness that he also falls madly in love with a local widow and millionairess? How do you feel about that man also being possessed of (and occasionally possessed by) a disturbingly violent temper? Does it help to know that his blood runs slightly cooler over time thanks to the gentling processes of love and grief? If you’re the type who can overlook this quality (and the disturbing ease with which you overlook it, yourself), in part because of how compelling his slightly pigeon-toed gait is as he stalks around the mining camp, you’re in the right place. The appeal of this gait cannot be explained, only observed and appreciated.

Your other flavor of Charming, Roguish Lawman is Deputy U.S. Marshal Raylan Givens, of the Harlan County Givenses, in Justified (and its one-season spinoff, Justified: City Primeval). Raylan is what you’d get if you combined Sheriff Bullock with this guy:

Am I wrong?

Raylan lacks Bullock’s starchy moral uprightness, and gets himself into all sorts of scrapes as a consequence. Still, it’s so much fun to watch him wriggle off the hook one season, only to launch himself right back at a whole row of hooks the next. And of course, there could be no Raylan without his nemesis/one true love, Boyd Crowder, with whom he famously dug coal when they were scarcely bigger than little tads.

He does love to wear a hat! N.B. Boyd’s nod to 19th century layering and accessorization

The last category of Timothy Olyphant character for today is the Full-On Himbo, a beautiful, if perhaps not brilliant, sort of fellow. Olyphant outgrew this type of role pretty early on, but it’s worth noting that the version of himself/Raylan he played in a few episodes of The Good Place is a sort of bridge between Charming, Roguish Lawman and Full-On Himbo.

That bridge could return us to a world where we encounter the silver foxy versions of Todd, the threatening yet I think ultimately harmless drug dealer from 1999’s Go or Sam from that 1998 episode of Sex and the City called “Valley of the Twentysomething Guys” in which he recounts a bizarre dream involving having enormous aluminum hands and crushing his enemies while Carrie was a beautiful unicorn woman with glass eyes before using the last of the TP as a coffee filter. Oh, dear. Cuteness only gets you so far (and does not make up for those alarming late 90s sideburns).

Share with a friend who can appreciate the fine distinctions across the subtypes of Charming, Roguish Lawmen.

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