Though Timothy Olyphant has made a career out of playing commanding lawmen, often in TV Westerns, two of his best roles are distinctly against type. After a few TV bit parts, including a memorable turn on Sex and the City, Olyphant rose to small screen prominence as Sheriff Seth Bullock in HBO’s acclaimed Western series, Deadwood. Not long after, the actor brought frontier justice into the 21st century in FX’s Justified, in which he played Deputy U.S. Marshal Raylan Givens, his most famous TV role to date.

It’s been awhile since Olyphant has headlined a Western — outside of 2023’s Justified sequel miniseries, Justified: City Primeval — but his TV career hasn’t slowed down at all, and he’s appeared in everything from Fargo to Daisy Jones & The Six to Alien: Earth. 2026 in particular has been a banner year for Olyphant, as he had starring roles in back-to-back hit summer series, Peacock’s The Five Star Weekend as Jennifer Garner’s love interest, Jack Finnigan, and Apple TV’s Lucky as Anya Taylor-Joy’s incarcerated con artist father, John Armstrong.

Though predictably good in both, he has much more to do in the latter, with Olyphant’s Lucky character actually quite reminiscent of his forgotten role in Damages. A legal thriller from FX, Damages centers on the complex and often toxic mentor-mentee relationship between ruthless veteran lawyer Patty Hewes (Glenn Close) and her whip-smart protege Ellen Parsons (Rose Byrne). Olyphant played Wes Krulik in seasons 2 and 3, he though he wasn’t on Damages long, he left a lasting impact on the series.

Damages Character Wes Krulik Is A Very Different Timothy Olyphant Role

Wes Krulik is first introduced in the Damages season 2 premiere when he meets Ellen at a grief counselling group. Ellen, who is mourning the loss of her fiancé, David, who was brutally murdered, is instantly drawn to Wes and things soon become more romantic between them. However, Wes isn’t all that he seems, as he isn’t really grieving a dead girlfriend; he’s been hired by the corrupt Detective Rick Messer, David’s killer, to keep tabs on Ellen. Things grow even more complicated when Wes falls for Ellen for real.

Essentially, Wes is the antithesis of the typical Timothy Olyphant TV character. Whereas Seth Bullock or Raylan Givens are on the right side of the law and almost always the man in charge, Wes is a deeply compromised character with little control over his life — or his emotions. For better or worse — and often worse — Wes almost always thinks with his heart over his head. It doesn’t do him or Ellen much good, but it certainly keeps things interesting, especially because he’s so unlike anyone Olyphant has ever played.

Wes Krulik Has A Lot In Common With John Armstrong In Lucky

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Over 15 years after his Damages arc ended, Olyphant would play another weaselly type in Lucky. Though John Armstrong came off like a much more recognizable Olyphant character — a slick smooth-talker in a leather jacket — he’s every bit as sketchy as Wes.

Like the Damages character, John is the protagonist’s closest confidante, advising Lucky even from jail. Just as Ellen has lost her fiancé, Lucky’s husband has vanished into thin air, taking $10 million in stolen cash with him and leaving Lucky on the run from both the FBI and the gangsters who want their money back. She has nobody to turn to but her father, and John weaponizes her vulnerability and the emotional intimacy of their father-daughter relationship in a remarkably similar way Wes did in his romance with Ellen.

However, the key difference between the two men is that Wes eventually falls in love with Ellen, and his motivations shift from betraying her to looking out for her best interests. John, on the other hand, doesn’t love his daughter nearly as much as he loves money and the art of the con. Olyphant’s Damages and Lucky characters are opposite sides of the same coin — but either way, Seth and Raylan certainly wouldn’t approve.