Prime Video's 'The Sexiest Man in Winnipeg' is a true crime train wreck — here's why it still fascinated me

Tom's Guide

13-05-2025

A Canadian sportscaster turned convicted felon with six bank robberies under his belt is one hell of a sales pitch for a true crime documentary. More brow-raising still is the fact that you get to hear how it all went down from the criminal himself.
Throw in a come-hither title like "The Sexiest Man in Winnipeg" and a voiceover from Will Arnett cast, somewhat bafflingly, as a bison, and it sounds like a true crime documentary engineered in a lab to generate buzz.
"The Sexiest Man in Winnipeg" landed on Prime Video last week (May 9). After watching it, I can tell you Prime Video's not challenging Netflix's place on the true crime throne anytime soon. But I enjoy dissecting documentaries as much as I do watching them to learn. Questions surrounding how the narrative is shaped, what context gets glossed over, or who is allowed a voice and who isn't are often more fascinating to me than the subject matter itself.
"The Sexiest Man in Winnipeg" is a case study in why these kinds of documentary ethics are so important, and as a nerd for that stuff, I couldn't take my eyes off this trainwreck as it was happening.
I can genuinely say it's unlike any other true crime documentary I've ever seen, but I'm not convinced that's a good thing. The closest comparison I can think of is if Netflix gave Tiger King the reins to make a documentary about his side of the story. Ill-advised? Absolutely. Entertaining? Debatable.
So if you're looking for a memorable watch, here's everything you need to know about Prime Video's latest true crime documentary.
Directed by Academy Award-nominated filmmaker Charlie Siskel, "The Sexiest Man in Winnipeg" follows the rise and fall of Steve Vogelsang. Once a fan-favorite sportscaster in Winnipeg back in the 1990s, he started making headlines for completely different reasons in 2017 when he was arrested for sticking up banks in Saskatchewan and Alberta.
Surprisingly, we learn much of this from Vogelsang himself, now a few years out from his six-and-a-half-year prison sentence. And he does much more than just tell his story. As narrator Will Arnett — playing a snarky talking bison that Vogelsang calls his "spirit animal" — says: This is a "true-crime documentary in which the criminal does his own reenactments.'
It quickly becomes clear why Vogelsang found success as a TV personality. He's a natural on camera, with a friendly, funny vibe that instantly connects with audiences. We see as much in the documentary's opening moments via old footage of Vogelsang in his prime, dressed sharp, full of charisma, and commanding attention as a local news anchor.
Interviews with former coworkers, students, family, and even his ex-wife paint a picture of a man respected in his field. Which is why his eventual fall from grace drew as much attention as the stranger-than-fiction facts of the case.
Also immediately apparent is that this is no career criminal we're dealing with here. That he managed to rob six banks before getting caught defies explanation. At one point, he describes holding up a bank with a glue gun made to look like the real deal, saying "I was more of a danger to bedazzle someone's jeans than shoot them."
In a gimmicky move that feels more tone-deaf than entertaining, Vogelsang teams up with the filmmakers to reenact his crimes, at times pretending to drive an invisible car, other times dressing up to mimic the blurry figures seen in old security footage.
Vogelsang earned the title that the documentary is named for from a local now-defunct magazine. At first, it comes off as a bit of cheeky irony, but as you learn more about his crimes, it takes on a much sinister tone.
My biggest frustration with "The Sexiest Man in Winnipeg" is that it gestures at the uncomfortable truths it raises without ever fully examining them. What could've been a powerful deep dive into mental health, media, and who gets to tell their story ends up caught between spectacle and indictment.
The filmmakers can't seem to commit to portraying Vogelsang as either a joke or a villain, settling instead on a milquetoast framing that punts the question to the audience to decide.
Arnett even says as much in the documentary: 'The filmmakers wanted to tell a good story, but they couldn't decide whether Steve was a hero or a villain, sympathetic or insincere, an unfeeling monster or a remorseful, complicated soul.'
It leans heavily on the outlandish elevator pitch and gimmick of Vogelsang being the one to recount his crimes. But when it comes time for Vogelsang to reckon with the fallout of his actions, he's lobbed softball questions. His victims are briefly mentioned but remain mostly anonymous, as the focus stays locked on Vogelsang himself.
Ultimately, it feels like Vogelsang is the one getting the last laugh. His initial crime spree came from a need to get back in the spotlight, and now we're talking about him once again. Which just left me thinking maybe this is one true crime story that should have stayed buried. I'm not interested in fueling this guy's narcissism, and I doubt many viewers will be thrilled at the chance to do so.