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Since the early days of his recording career, the late Canadian singer-songwriter Leonard Cohen has played a key part in some of film and TV’s most spellbinding moments. Robert Altman’s McCabe & Mrs. Miller (1971) is so inextricable from the three Cohen songs that recur throughout – ‘The Stranger Song’, ‘Sisters of Mercy’ and ‘Winter Lady’ – that it’s hard to believe they weren’t originally written for the sequences in question (they’d appeared on Cohen’s debut album four years earlier). Atom Egoyan, a compatriot of Cohen, has cited the song ‘Everybody Knows’ as intrinsic to the tone and ideas of his own puzzle-box drama Exotica (1994), while that same year, Olivier Assayas made beautiful use of Cohen’s ‘Avalanche’ in the extended party set-piece of Cold Water, where it scores the long-gestating first kiss between two close teenage friends. This isn’t to mention the various covers of Cohen that have made their way onto soundtracks: new generations were introduced to the man through recordings of ‘Hallelujah’ by John Cale and Jeff Buckley, in Shrek (2001) and teen drama series The O.C. (2003-07) respectively.

With all this in mind, any filmmaker producing a fiction feature based entirely around Cohen songs – bar original score compositions and the occasional diegetic background tune – is setting themselves up for potentially unfavourable comparisons. That’s what writer-director Matt Bissonnette has on his hands with Canadian-Irish co-production Death of a Ladies’ Man (2020), named after Cohen’s 1977 studio album and incorporating seven songs from across his career: ‘Hallelujah’, ‘Bird on the Wire’, ‘Memories’, ‘Why Don’t You Try’, ‘Heart with No Companion’, ‘Did I Ever Love You’, and Cohen’s rendition of ‘The Lost Canadian (Un Canadien errant)’, a mid-19th-century folk song. Cohen’s poem ‘The Music Crept By Us’ also gets recited during one of the film’s many fantastical flourishes, while chapter cards quote his lyrics.

This isn’t Bissonnette’s first flirtation with Cohen on film. ‘Suzanne’ featured in his 2009 effort Passenger Side, while a far more explicit motif was present in Looking for Leonard (2002), which, as well as using footage taken from 1965 documentary Ladies and Gentlemen… Mr. Leonard Cohen, sees one protagonist falling in love with Cohen’s novel Beautiful Losers, entertaining fantasies of meeting and running off with the artist for a more fulfilling future.

In Bissonnette’s darkly comic new movie, Gabriel Byrne plays alcoholic Montréal-based professor and titular ladies’ man Samuel O’Shea. As his second marriage breaks down, O’Shea learns he may not be long for this world after a series of hallucinations leads to him getting his head examined and subsequently being diagnosed with an inoperable brain tumour. We are party to the hallucinations: the first takes place in the moments before a hockey game in which his son Layton (Antoine Olivier Pilon) is playing, where a microphone-wielding young woman set to perform the national anthem breaks instead into ‘Bird on the Wire’. Sam is the only one to notice this, just as he’s the only one to see both hockey teams bursting into ballet moves on the ice.

Death of a Ladies’ Man doesn’t turn into a full jukebox musical in the vein of Julie Taymor’s Beatles film Across the Universe (2007), but the hockey sequence is the first of several lip-synced musical montages. Aside from song-and-dance confections, Sam’s hallucinations also include such sights as a bikini-clad waitress with the head of a tiger and, for a stretch of the film, an entirely fabricated new companion. The most recurrent visions comprise extended conversations with his long-dead father (Brian Gleeson), visually presenting as the young age at which he had died. Gleeson’s charismatic confidant ghost is thankfully free of the computer-generated embellishments that elsewhere draw attention to the film’s budgetary constraints, such as when Sam sees fire-breathing geese obliterating Montréal.

There’s a degree of whimsical fun to proceedings for a while, helping leaven the dark subject matter. But patience with the film’s structural messiness wears thin as a 20-minute Ireland-set portion of the film’s middle is undone by a cheap twist and an unintentionally farcical drop of ‘Hallelujah’. The film’s opening shot, set to ‘Memories’, is of Montréal’s large Cohen mural on Crescent Street gradually coming into focus, suggesting that the artist’s work will directly inform what follows. But beyond broad notions of personal torment and how it affects others, Bissonnette’s curation of tracks doesn’t seem relevant to the narrative, especially the bizarre crime-thriller detours. The film’s very raison d’être is unclear: it never comes across that these songs are truly necessary to this scattershot story.

► Death of a Ladies’ Man is available to stream on a range of platforms now.