Steve Vogelsang is the subject of a new Prime Video documentary, “The Sexist Man in Winnipeg.” (PRIME VIDEO)
It’s an unassuming, yet intriguing title for a true crime documentary — “The Sexiest Man in Winnipeg” — that takes you on the roller coaster life of Steve Vogelsang, a former Winnipeg news personality who once had it all.
The Prime Video documentary, which begins streaming on Friday, is directed by Academy Award-nominated filmmaker Charlie Siskel and Ben Daughtrey, who also edited the film.
The film delivers a provocative yet uneven documentary that explores the rise and fall of Vogelsang — once a respected journalist at CKY (now CTV Winnipeg) and journalism professor at Red River College, later a convicted bank robber. What could have been a searing investigation into mental health, masculinity, and media legacy instead wavers between sensationalism and sympathy, unsure of whether to indict or eulogize its subject.
The documentary opens with archival clips of Vogelsang at the height of his career: sharp-suited, charismatic, and commanding attention as a local news anchor. Interviews with former colleagues, students, and family members (including his ex-wife) paint the early portrait of a man admired for his confidence and talent. The title, drawn from an honour once bestowed on Vogelsang by a local now-defunct magazine, initially feels like playful irony but grows increasingly jarring as the film unfolds and Vogelsang’s criminal history comes into focus.
As Vogelsang reenacts some of his crimes for producers, he admits he doesn’t often reminisce about what he did. But wrapping up his hand in toilet paper and smearing ketchup on it to mimic a similar bandage he wore on his hand during one of his robberies brings an uneasy feeling to the viewer.
Where the film succeeds is in its ability to generate unease — not from its subject’s criminal actions alone, but from the dissonance between who Vogelsang was and who he became. His transition from educator to fugitive is presented with minimal narration by Canadian actor Will Arnett, who tells the story from a bison’s perspective. In the opening minutes of the film, Vogelsang refers to the bison as his “spirit animal,” allowing the audience to absorb the contradictions for themselves.
But the film’s weaknesses lie in its tone. At times, it leans too heavily on charm and nostalgia, allowing soft-focus recollections to overpower harder truths. While some interviewees question the choices Vogelsang made and the harm caused, these critiques are often undercut by the film’s stylistic choices — a wistful soundtrack, cheesy cutaway b-roll, slow pans over old photos, and a reluctance to press deeper into the darker corners of the story. The victims of his crimes are mentioned, but largely left faceless, as the narrative continues to orbit the enigmatic figure at its centre. That’s one regret Vogelsang admits to as far as his non-paid participation in the film, in which his victims will forever live with the trauma he caused them during his robberies.
“The people that I hurt, that I scared, that I shocked, that I disappointed… they at least deserve something of a happy ending,” Vogelsang says as the film draws to a close.
“Everybody will feel better if this has some sort of positive ending. ‘Well, in the end, Steve helped some people, so it wasn’t a total loss.'”
Ultimately, The Sexiest Man in Winnipeg stops short of fully interrogating the uncomfortable truths it raises. It’s a film that remembers the man he was, flinches at the man he became, and leaves the viewer wondering: is this redemption, reckoning, or just reflection?
Vogelsang was sentenced to 6.5 years in prison for his crimes committed across Saskatchewan and Alberta in 2017. He was released in 2022 and now lives in Penticton, B.C.
