Brody Jenner’s enduring Hills legacy? No doubt that thousand-watt smile, but like the Cheshire Cat’s, it could occasionally hide something unexpectedly sinister (at least a little bit sinister).

By the end of the show’s six-season run, Brody had evolved from a no-worries playboy into a good pal and a reliable shoulder to cry on. Still, he’d paved his path across Los Angeles with a good bit of troublemaking too: Between taunting Stephanie Pratt, landing in jail and making a Playboy Bunny lose her mind, Brody proved he had some tricks up his sleeve and could definitely deviate from the relaxed West Coast prototype that typically made him a fan favorite.

It goes without saying that — more than a decade after the premiere of The Hills — Brody has matured, but isn’t it fun to explore the sins of our youth? Check out Brody’s five most scoundrel-like moves across The Hills below, and hang tight for more info on New Beginnings, which will reintroduce us to he-with-“Brittany Canada Whore”-in-his-iPhone-contacts.

Jen Bunney Blues

Sure, Spencer engineered the hookup that created some unforgettable Hills drama, but it was Brody who followed through with the encouragement. Though the Prince of Malibu was dating *a particular leading lady* of the show, he — no doubt with some liquid encouragement — hooked up with one of her friends. JB bore the brunt of the blowback, and somehow, Brody got off almost scot-free.

He Made Jayde Crazed

Later on in the series, while Brody was dating Jayde, *another particular leading lady* came back to town and threatened the relationship. Though Brody never cheated, he couldn’t convince Jayde that he and his ex were over, and it led to more fights than any referee could manage.

McKaela Mayhem

When McKaela first appeared on The Hills in Season 6, the Smashbox employee seemed like somebody you could root for. And Brody thought the same…until he didn’t. Though he seemed like he was into McKaela when the two started dating, he quickly reverted to some of his old gameplay and hung her out to dry.

Stomping All Over Stephanie

Though Brodes typically got along with his fellow Hills clique, he and Stephanie could never seem to find peace, and at some points, Brody went as far as to taunt Spencer’s little sister for what he called crazy behavior. Finally, he straight up told the eventual People’s Revolution assistant that she was unwelcome in his social circle, sending her into a deluge of tears. Uhhhh, yikes.

Landing in the Slammer

Yup, in the very same episode that found Brody going toe-to-toe with Stephanie, he and his pal Doug landed in jail for a fight in a Las Vegas bar. Basically a rite of passage for the Hollywood elite, no?

See Ya, Spencer

Okay, so this was more Spencer’s fault — he told Brody that as long as he hung out with Spencer’s “enemy,” the two couldn’t be friends. Still, Brody took the feuding and ran with it, eventually calling Spencer a shameless attention-seeker any chance he got. Brody also famously told Spencer he’d “lost it” after cultivating that oh-so-identifiable crystal fixation.