'The Sexiest Man in Winnipeg': True crime film tells odd story of sportscaster-turned-bank robber

Yahoo

21-05-2025

In the documentary The Sexiest Man in Winnipeg (now on Prime Video), narrated by Will Arnett, directors Ben Daughtrey and Charlie Siskel chronicle the odd true crime case of broadcaster-turned-robber, Steve Vogelsang. The beloved sports anchor confused locals when he was found to have led a number of odd bank heists.
For Daughtrey and Siskel, it's the character study component of Vogelsang's story that interested them. With a "made for TV personality" — Vogelsang even reenacts his own crimes for the documentary — it's a fascinating film that brings up several questions about fame and celebrity.
"I don't think either of us has a particular interest in true crime as a genre, but this was an opportunity to take it apart as a form, and break it open and look at the true crime industrial complex that we seem to all feed on," Siskel told Yahoo Canada.
While Vogelsang's crimes weren't victimless, with traumatized bank employees impacted by his actions, the heists were so mishandled and executed without strategic thinking that they're more like heists you would see in a comedy movie, not real life.
"When you look at Steve's crimes, his half a dozen robberies, he created characters for each of these crimes," Siskel highlighted. "They were theatrical, they were performative. They're funny. He's got little jokes in them."
"He hid the money that he stole from one of the banks inside an urn with his mother's ashes. Did he have to do that? Was that the best hiding place? Or was it something that would make a great story to tell afterwards."
But all of that also feeds into is Vogelsang's desire for attention.
"He's a media animal," Siskel said. "As a kid, his mother called him, 'My son the Prime Minister.' This was a guy who knew his way around storytelling."
"He made himself kind of a centrepiece of a lot of the sports stories he did. So it seemed fitting to kind of take him apart as a character, as someone who didn't want to live an ordinary life. Steve got quite used to being a celebrity, lost that celebrity, and I think we kind of asked the provocative question, is it possible that Steve robbed a bunch of banks in order to tell a great story. In order to become a celebrity again, in order to have ... another crack at fame?"
Going one step further, The Sexiest Man in Winnipeg also becomes an evaluation of its audience, and the filmmakers. There's a moral question about how we create and consume crime stories as entertainment.
"We wanted all of that complexity, moral complexity, narrative complexity, and allow the audience to be jury members and decide what they think of it," Siskel said. "What do they think of Steve as a character? What do they think of the filmmakers? What do they think of themselves as consumers of this kind of entertainment? And hopefully have a lot of laughs too. Sometimes at Steve's expense, because he is quite willing to play the fool, I would say."
What's brought up in The Sexiest Man in Winnipeg is who the "real" Vogelsang is, and what's just a facade or a show. When asked if the directors believe they got to know the real Vogelsang, they identity him as both a "publicity monster" and "a human being trying to figure out who he is."
"I think both things are equally true, and that's what we're trying to do with the film," Daughtrey said.
"I think Steve maybe grew in some ways over the course of the film. I think Charlie and I were like, at moments, 'God, I hate this guy.' And then other parts of us were like, 'I sort of empathize with him.'"
Vogelsang also claims in The Sexiest Man in Winnipeg that he didn't enjoy fame very much, but the filmmakers aren't so sure, and the audience is likely to be dubious of that statement as well.
"Steve is hyper-intelligent and he's super delusional, in my opinion, and he has an answer for everything," Daughtrey said. "Some days I believe him, some days I don't."
"Clearly where he ends up is quite modest, but maybe that's just a fault of his life choices."