Henry Cavill Called Himself a Sellout—And No One Blinked. Why?

There’s something about early 2000s romantic comedies that keeps fans coming back for more—especially when the stars themselves start sharing never-before-heard stories from behind the scenes. Ryan Reynolds, now known worldwide as the wisecracking antihero Deadpool, once ruled the rom-com genre, and it turns out his off-screen antics during the filming of Just Friends (2005) nearly landed him in serious trouble with the law.

Reynolds recently recounted the prank on the “Conan O’Brien Needs a Friend” podcast, revealing how close he came to swapping his movie set for a jail cell. Filming in Regina, Saskatchewan, Reynolds teamed up with the art department to pull a stunt that could have gone sideways fast. “It’s one of my few times that I’ve ever been scared of going to jail,” Reynolds admitted. “Just as a joke, me and the art department, we made a sign that would go over, it would snap over the ‘Welcome to Regina’ sign. And it just said ‘Welcome to Regina, which rhymes with fun.’ And I got in trouble though.”

The joke earned hearty laughs from Conan O’Brien and his crew, but at the time, Reynolds faced the real possibility of being charged with vandalism. “At first it was vandalism, and then it was class,” Reynolds quipped, noting that the city’s officials ultimately found it more amusing than criminal. Since the sign wasn’t permanent—“it snapped off”—the prank was later considered more of a fleeting art installment than a punishable offense. O’Brien observed, “It became an art installment that could come down.”

For fans, the story adds another layer of charm to Just Friends, which follows Reynolds’ character Chris Brander as he returns to his hometown to win over his high school best friend Jamie (Amy Smart) after years of awkward friend-zoning. The film also stars Anna Faris, Chris Klein, Christopher Marquette, and Julie Hagerty. Though Just Friends wasn’t a hit with critics (earning a 42% score on Rotten Tomatoes and a 47% from TV Guide), it grossed over $50 million at the box office and has grown a devoted following in the years since.

As Reynolds proves once again, sometimes the most memorable moments happen when the cameras aren’t rolling—and the threat of jail time is just another funny chapter in the actor’s storied career.