Former Red Wings players Sean Avery and Chris Chelios appear in the movie Happy Gilmore 2, very briefly, as mafia henchmen:
Sean Avery and Chris Chelios had a brief cameo in ‘Happy Gilmore 2’ serving as a gangster’s henchmen.
— B/R Open Ice (@BR_OpenIce) July 28, 2025
Avery racking up those IMDB credits like penalty minutes 😂 pic.twitter.com/Sng9RIxwXY
Detroit Hockey Now’s Bob Duff explains:
Adam Sandler may be decked out in a Boston Bruins jersey as the star of Happy Gilmore 2, but a couple of former Detroit Red Wings are the ones representing the NHL in the hit film.
Sandler portrays a hockey player turned golfer, but it’s ex-Red Wings Sean Avery and Chris Chelios who are hockey players turned actors on screen.
Well, actors might be a bit of a stretch. Extras would be the more appropriate acting handle to apply to their cameo roles on screen.
Billing in the credits shows them as Henchman #1 (Avery) and Henchman #2 (Chelios). The two former hockey stars feature briefly in a black and white scene, serving as the muscle for a 1950s-era gangster. Chelios appears especially impressive in his role, looking as though they were lifting him straight out of an old George Raft gangster flick. Don’t blink or you might miss it, though.
