Hero or villain? Documentary can't decide

Winnipeg Free Press

08-05-2025

Centring on the stranger-than-fiction saga of former Winnipegger Steve Vogelsang, this alternately intriguing and exasperating hybrid documentary tracks his trajectory from onetime local TV personality to convicted bank robber.
As many Winnipeggers know, Vogelsang found fame and fortune here in the 1990s as a sportscaster for CKY (later CTV). In 2017, he became the talk of the town — in a very different way — when he was charged with committing a string of robberies across western Canada.
In one sense, this crime story is as Winnipeggy as honey-dill sauce. In another sense, it's not that Peg-specific at all. Basically, the film uses Vogelsang's bizarre, breaking-bad bio as a pretext to raise questions about what documentaries can and cannot do.
American filmmakers Charlie Siskel (Finding Vivian Maier) and first-timer Ben Daughtrey want to examine the nature of truth, the lure of narrative and the complicated relationship between filmmaker and subject. Documentarians such as Joshua Oppenheimer, Alex Gibney and Errol Morris regularly and seriously raise these issues in their works.
Unfortunately, The Sexiest Man in Winnipeg never makes good on its premise. This is the lite version of cinematic introspection.
To start off, there's that cute, come-hither title, which derives from the results of an Uptown magazine readers' poll. There's the misplaced determination — especially at first — to frame Vogelsang's crime spree as a jaunty, comical caper, even though his actions did real harm to real people.
And there's the voiceover narration. Comedian and actor Will Arnett, the Arrested Development alumnus who has Winnipeg family connections, relates Vogelsang's story, which makes sense.
But the decision to present Arnett as a slightly snarky talking bison? That's just bad.
Putting all this strained, gimmicky stuff to one side, Vogelsang can be a compelling subject. At one point, he says there are people who judge you on the worst thing you've ever done and people who judge you on the best thing you've ever done. As the filmmakers speak with Vogelsang's colleagues, students, family and friends, the doc aims to span that spectrum.
One can immediately see why Vogelsang succeeded as a TV personality. He's a natural performer, with an onscreen persona that comes across as affable, relatable and funny, and he was good at connecting with viewers. Back in the day, he had a wardrobe supplied by Harry Rosen. He MC'd local charity dinners and events. He was 'Winnipeg famous.'
Steve Vogelsang was a TV sportscaster in the 1990s.
Steve Vogelsang was a TV sportscaster in the 1990s.
Sensing that his time in front of the camera was coming to an end, Vogelsang became an instructor in broadcast journalism at what was then Red River College (now RRC Polytech). There he performed for his students, many of whom talk of him as an inspiring and supportive teacher.
But even at the peak of Vogelsang's good times, there are hints about how things might go wrong. There's his seemingly bottomless need for external attention and validation and his tricky combo of arrogance and insecurity. Add in depression, debt and divorce, plus some plot twists involving family history and personal relationships, and Vogelsang's life takes a sudden, drastic turn.
Through archival news footage and extensive talking-head interviews, including with all-round sports guy Peter Young and Free Press reporter Melissa Martin, the film offers different, even conflicting takes on Vogelsang.
Then there's Vogelsang's own take, which brings up Daughtrey and Siskel's decision to put the man himself at the centre of the documentary process.
As our talking-bison friend suggests, this is a 'true-crime documentary in which the criminal does his own reenactments.'
Vogelsang collaborates with the filmmakers to act out his crimes, sometimes driving around in an imaginary invisible car, sometimes dressing up to replicate grainy security videos.
Winnipeg Jets Game Days
On Winnipeg Jets game days, hockey writers Mike McIntyre and Ken Wiebe send news, notes and quotes from the morning skate, as well as injury updates and lineup decisions. Arrives a few hours prior to puck drop.
Vogelsang at first tries to downplay what he did. He didn't make that much money. He didn't consider himself violent because he didn't use actual weapons.
At one point, he held up a bank with a disguised glue gun.
'I was more a danger to bedazzle someone's jeans than shoot them,' he says, a joke that tries to paper over the fact that even if the 'guns' were fake, the tellers experienced the threat as real.
As Vogelsang attempts to come to terms with the trauma he caused, the film becomes a more complex and serious exploration of identity.
It also raises some knotty issues about documentary ethics. If, as some interview subjects suggest, Vogelsang's crimes came from a need to get back into the spotlight, could the film itself be a continuation of what one interview subject calls Vogelsang's 'celebretization of himself?'
As Martin suggests, 'I think one of the tricky things in this story is to remember that in some way Steve is always going to be trying to control the narrative.'
At several points, Vogelsang says he co-operated with the film because he hopes people can learn from his mistakes.
But what have we learned by the end of this project?
Viewers might be looking for closure, for a satisfying character arc, for a journey of self-knowledge, self-improvement or maybe even redemption.
The film seems to resist. By the end, The Sexiest Man in Winnipeg feels like a warning about the limits of documentary storytelling. As the bison ruefully tells us: '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.'
So, you'll have to decide about Steve Vogelsang for yourself. You'll also have to decide whether this open-ended documentary approach is refreshingly honest or just frustrating.
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Alison GillmorWriter
Studying at the University of Winnipeg and later Toronto's York University, Alison Gillmor planned to become an art historian. She ended up catching the journalism bug when she started as visual arts reviewer at the Winnipeg Free Press in 1992.
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