1 Year Before Justified, Timothy Olyphant Starred in This Underseen 83% RT Heist Flick

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Timothy Olyphant is incredibly versatile, consistently demonstrating his acting range across different genres. He quickly showed he could avoid being stuck in one type of role – something many actors struggle with for years. While he became well-known as a Western star in the 2000s thanks to shows like Deadwood, he’s also delivered amazing performances in very different kinds of movies and TV shows. He’s particularly good at comedy, as seen in his lead role as Dick in the 2009 film High Life.

Timothy Olyphant’s film High Life is surprisingly overlooked, especially considering his other work. It’s different from the 2018 science fiction film of the same name; this earlier High Life is a Canadian comedy about a simple robbery that quickly spirals out of control. The 1980s-set film, directed by Gary Yates, centers around a group of drug addicts who attempt to rob newly installed ATMs. The movie helped launch Olyphant’s career in comedy, leading to more comedic roles and establishing him as a popular comedy actor.

High Life Shows the Mess Made by Four Drug Addicts Who Get Ambitious

High Life is a comedy that looks at the flawed lives of people struggling to find their place during the 1980s, a time when consumerism was booming in America. The film is based on a play by Lee MacDougall, who also adapted it for the screen and was nominated for a Genie Award in 2011 for his writing. High Life first shown at the Berlin International Film Festival in 2009, and later that year, it won the award for Best Canadian Feature at the Calgary International Film Festival.

Critics, including Johanna Schneller, have hailed it as one of the best films of 2010. Though it received positive reviews when it was released and has gained renewed attention since, the movie remains somewhat underappreciated. While High Life isn’t necessarily a comedy or known for its script, its smart storyline is still engaging and deserves a wider audience. Fans of Timothy Olyphant, in particular, will enjoy his excellent performance.

The film centers around four people struggling with drug addiction who decide to rob a bank, but their plan quickly falls apart. Timothy Olyphant stars as Dick, a hospital maintenance worker trying to rebuild his life after being released from prison. His old cellmate, Bug (played by the late Stephen Eric McIntyre), unexpectedly reappears at Dick’s job right after getting out of prison. Bug immediately causes trouble by smoking and stealing medical supplies, which results in Dick losing his job.

Walking back to Dick’s place, Bug notices how much the world has changed since he was in prison, especially new ATMs that let people get cash directly without a bank teller. This conversation sparks an idea in Dick: a simple robbery targeting an ATM, since it wouldn’t involve anyone getting hurt. However, the plan is risky because Bug is volatile, grappling with personal issues, and quick to resort to violence if challenged.

Dick assembles a heist crew by enlisting two fellow addicts. He meticulously plans a scheme to deceive local workers and steal machinery. Rossif Sutherland plays Billy, a likable man Dick meets in a Narcotics Anonymous group. Joe Anderson portrays Donnie, an acquaintance of Dick and Bug from their time in prison. The four men gather to use crushed morphine pills and listen to Dick’s plan, which they all accept. Each member of the crew has their own unique personality, but Dick, played by Timothy Olyphant, is particularly memorable. Olyphant’s performance is a striking departure from roles he took on just a year later; he’s almost unrecognisable as this disheveled and desperate morphine addict who clearly needs to clean up. While Olyphant often brought a comedic touch to his performances at the time, taking on this role in High Life was a bold move that proved successful.

Timothy Olyphant Pursued More Comedy Roles After High Life

I’ve always admired how Timothy Olyphant jumps between all sorts of roles – he’s not afraid to try anything! He actually started on stage, and right out of the gate, he was a hit! He won an award for his very first play, The Monogamist, back in 1995, which quickly got him noticed in Hollywood. He didn’t start with leading roles, though. His first movie part was a funny, irritating director in a 1996 comedy – you could already tell he was great at that kind of thing. Then he started popping up in bigger projects, like being the unexpected villain in Scream 2 and even doing a guest spot on Sex and the City.

Timothy Olyphant first gained significant comedic recognition in 1999 with roles in the independent film No Vacancy, alongside Christina Ricci, and as a drug dealer in Go. He continued to work in various genres throughout the early 2000s, including action and romance. However, his career really took off in 2009 when he starred in the dark comedy High Life – his first leading role in a non-romantic comedy – marking a turning point in his career.

Even before High Life, he was already a major star, especially after [previous work]. But he kept getting cast as either the tough guy or the romantic lead – sometimes both at once! That’s why playing Dick, a troubled addict lost in his own world, felt so different and exciting. It was a really interesting turn for him, and honestly, a much more complex role than anything he’d done before, even compared to the drug dealer characters in films like Go and A Man Apart.

Before High Life, Timothy Olyphant really started to break out with Deadwood. That show, which premiered in 2004, made him a genuine TV star before he became a leading man in films. It was the first time he felt like he could move beyond being typecast. You see, before Deadwood, as Vulture’s Matt Zoller Seitz pointed out, I always saw him as that ‘funny bad boy’ type. But playing Seth Bullock, a truly righteous character, was a huge shift and really showed what he could do. Even after that, though, he often ended up playing either the charming heartthrob or, you guessed it, another bad boy – until High Life came along.

Following the film Hitman, Variety critic Todd McCarthy praised Timothy Olyphant as an actor who could convey nuance and intelligence, encouraging him to take on more diverse roles. Olyphant agreed, telling The AV Club in 2010 that working on Hitman changed how he approached choosing projects. He explained that while he enjoyed working with the director and crew, he began to question the types of roles he was accepting, and felt motivated to be more selective and thoughtful about his career.

After appearing in High Life and gaining recognition for his work on Justified, Timothy Olyphant started taking on more comedic parts. Throughout the six seasons of Justified, he also made guest appearances on comedy shows like The Mindy Project, demonstrating a previously underappreciated talent for humor. He eventually became known for his excellent comedic timing and his knack for adding a touch of humor to even dramatic roles.

While he’s best known for Westerns, action films, and dramas, this actor has a real knack for comedy, and his fans appreciate that side of him. For over ten years, he’s been consistently sought after for comedic roles, both big and small. He really shone in projects like the 2013 film Dealin’ with Idiots, the 2014 film This Is Where I Leave You, the 2015 TV series The Grinder, the 2016 play Hold On to Me Darling, and the 2017…

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2025-11-09 02:07