The Sexiest Man in Winnipeg documents a broadcaster-turned-bank robber. That doesn't make it interesting

CBC

07-05-2025

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Stop me if you've heard this one. A Canadian sports broadcaster walks into a bank. He's cradling a bleeding hand, wearing a bomb and smiling a crooked smile.
"Hi," he says. "I'm TV's Steve Vogelsang. Hand over everything in the till."
OK, maybe he didn't use those exact words.
But according to The Sexiest Man in Winnipeg, Vogelsang's real-life robberies did, more or less, follow those beats. And the documentary — premiering Friday on Prime and made with Vogelsang's co-operation — markets itself as following that bizarre spree; a descent from CKY Winnipeg's supposedly fan-favourite 1990s onscreen jokester, to a 2010s convicted felon with six bank robberies spanning two provinces.
Astoundingly, we learn much of this from Vogelsang himself — a few years after his six-and-a-half year prison sentence, and seemingly more than game to re-enact the various crimes he orchestrated at banks between Alberta and Saskatchewan.
WATCH | The Sexiest Man in Winnipeg trailer:
But as he narrates how he built the fake bomb in a nearby motel room and even why he once went for a facial immediately after a stickup, the question, of course, becomes "Why?"
Why would a successful, well-liked and seemingly normal journalist suddenly — to steal a Vince Gilligan-ism — break bad?
In keeping with that AMC show, part of the reason may be that he was never all that normal. The by-then divorced, twice-retired (from journalism and then teaching) enigma at the centre of our story is perhaps not all that difficult to unravel. He's prickly; he's self-assured to a fault and impulsive. He received a no-contact order for a student he dated; he once told his ex-wife — while they were still married — he would forever remain the smartest person she'd ever met.
But that's about where the twists and turns end. We get an intriguing opening, detailing Vogelsang's often cinematic robbery plans, and we hear from more than a few people who actually knew him. There are his students, ex-wife and the cops and prosecutors tasked with catching him. There's even the slick narration of Will Arnett, perpetually dwelling on the strangeness of both the case, and Vogelsang's participation in the documentary.
Though, perhaps somewhat confusingly, Arnett is cast as a bison, telling the story in a tongue-in-cheek voiceover that frequently cuts to images of the animal as if it's the one telling the story. It's a frustratingly artificial conceit, seemingly chosen to both tie in to the general tone of the documentary and, as Vogelsang explains in a pointedly unexamined remark, because the misunderstood brutes are his "spirit animal."
In short, neither our star or story are, as Shrek would say, like an onion: The Sexiest Man in Winnipeg is critically short when it comes to layers. There's even a depressing lack of novelty. Like how band Flight of the Conchords often jokingly described themselves as New Zealand's fourth most popular guitar-based digi-bongo acapella-gangsta-rap-funk-folk comedy duo, Vogelsang is a runner-up even in the incredibly niche genre he's created for himself.
When it comes to the most famous Canadian late '80s/early '90s ex-performer-turned-bank-robber, subsequently starring in a streamer-released documentary about their time in prison and subsequent rehabilitation, Vogelsang is, at best, number two.
The winner would probably be actor Deleriyes (Joey) Cramer (Flight of the Navigator). But where his documentary, Life After the Navigator, effectively mines his pathos and self-reflection, The Sexiest Man in Winnipeg is seemingly more interested in the story's elevator pitch than its substance.
Lack of depth
This is particularly disappointing given who's behind the project. Co-director Charlie Siskel (who worked with first-timer Ben Daughtrey) is perhaps best known for the Oscar-nominated documentary Finding Vivian Maier, about the curiously dark life of a prolific and previously unknown street photographer.
And like his followup doc American Anarchist — about the somewhat regretful author of bomb-making manual The Anarchist Cookbook — his work succeeded by the depth he found in his subjects.
Maier first appeared to be a normal nanny, then an outsider artist, and then a deeply unwell victim of unmanaged mental health issues. American Anarchists 's William Powell was first a countercultural iconoclast, then a reluctant apologist — alternatively lamenting his book's association with violent crimes, and sparring with Siskel as he pushes him to declare his own guilt.
But deprived of the incredible complexity of Maier, and perhaps wary of criticism he received for the combative tone of American Anarchist, any interest The Sexiest Man in Winnipeg might offer expires about 20 minutes in. Why did Vogelsang rob those banks? Because he needed money. Isn't there a deeper, more intriguing motivation? To be honest, not really. This was years after his journalism career — during which he was a hyper-local sort of celebrity, cannibalized by an industry shrinking fast enough you'd be harder pressed to find people therein without financial problems than with them.
This is why the premise of the documentary — that Vogelsang is somehow an absurdly odd "type" of bank robber — soon falls flat. He was an aging, out-of-work man whose talents lay in a dying field. Any assumption about what the typical criminal looks like, and Vogelsang's apparent distance from it, springs from potentially harmful stereotypes.
After those aspects are dealt with, The Sexiest Man in Winnipeg becomes a long apology video — a tenuous excuse to exist, especially given Prime already told one niche, offbeat Canadiana crime story with its recent maple-syrup heist miniseries, The Sticky.
And even still, whether Vogelsang has earned any redemption is irrelevant. The true feelings in his soul are beyond the scope of a documentary, let alone a review. But aside from a late and tenuous revelation around an old family friend's possibly negative influence on Vogelsang, there are few depths to plumb. And without them, the majority of this documentary amounts to a platform for Vogelsang to make the case that he's sorry.