Happy Gilmore 2 cameo list includes Stephen A. Smith

Happy Gilmore 2 cameo list includes Stephen A. Smith originally appeared on Athlon Sports.

Nearly three decades after the cult classic 'Happy Gilmore' first hit screens in 1996, Adam Sandler is back with 'Happy Gilmore 2', and the sequel is already making waves thanks to its star-studded list of cameos, including none other than ESPN’s outspoken personality, Stephen A. Smith.

Known for his hot takes and animated delivery, Smith is set to bring his trademark style to the golf world in what promises to be one of best scenes of the feature film.

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In Happy Gilmore 2, Sandler reprises his iconic role as Happy, the hockey player-turned-golf phenom whose life has taken a darker turn since his improbable Tour Championship victory over Shooter McGavin (Christopher McDonald).

Following a tragic accident in which Happy’s overly powerful drive kills his wife, Virginia (Julie Bowen), Happy has spiraled into financial ruin and personal grief. With five kids to care for, sons Gordie (Maxwell Jacob Friedman), Bobby (Philip Schneider), Wayne (Ethan Cutkosky), and Terry (Conor Sherry), plus daughter Vienna (Sunny Sandler), Happy makes a desperate return to golf. His comeback pits him against shady businessman Frank Manatee (Benny Safdie) and the villainous Billy Jenkins (Haley Joel Osment), the star of Manatee’s outrageous stunt-based golf league, Maxi Golf.

This is where Smith steps in. Appearing as himself, Smith delivers over-the-top commentary on Happy’s unexpected resurgence during the Tour Championship. He initially hypes Happy’s two-day success, only to gleefully tear him down after his third-day collapse. The elements fit seamlessly into the chaotic, absurd world of Happy Gilmore.

The cameo lineup doesn’t stop there. Golf legend John Daly is hilariously cast as himself, now living in Happy’s garage during retirement. WNBA star Kelsey Plum and producer Andrew Watt pop up as quirky starters at Happy’s local municipal course, while sports media icon Dan Patrick hosts Sports Hole with Pat Daniels, breaking the news of Happy’s drunken escapades. Kansas City Chiefs tight end Travis Kelce even makes a comedic turn as a waiter desperate to impress the Tour Championship golfers. Here's a full list of cameos for 'Happy Gilmore 2' via Time Magazine.

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Longtime CBS sportscaster Verne Lundquist also returns, joining Jack Beard to call the action, while pro golfers like Rory McIlroy, Brooks Koepka, Bryson DeChambeau, and Scottie Scheffler add star power to the tournament scenes.

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'Happy Gilmore 2' is now streaming on Netflix. It's shaping up to be a must-watch mix of nostalgia and humor.

This story was originally reported by Athlon Sports on Jul 25, 2025, where it first appeared.