KROQ Almost Acoustic Christmas, 1994
Jordan Catalano, My So-Called Life: Jared Leto’s turn as Jordan Catalano, heartbreaker extraordinaire, launched his career and solidified his spot as one of pop culture’s favorite heartthrobs.
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Christian Slater
James “JD” Dean, Heathers: Christian Slater as Winona Ryder’s alluring, but slightly disturbed partner-in-crime in the cult dark comedy Heathers had us all wondering if they were headed to jail or to the prom.
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Lauren Conrad Exclusive Fashion Week After Party – Arrivals
Stephen Colletti, Laguna Beach: Laguna Beach’s bad boy was responsible for most of the drama on the eponymous reality tv show and the still-standing Lauren Conrad and Kristin Cavalleri rift that spanned nearly a decade of MTV.
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Milo Ventimiglia Portrait Shoot
Jess Mariano, Gilmore Girls: The dark horse of Stars Hallow, Jess Mariano (played by Milo Ventigmigalia), proved to be Rory’s intellectual equal and a worthy love interest (despite being a terrible boyfriend). The bad boy charm wasn’t only limited to the small screen — Ventigmigalia and Rory’s Alexis Bledel dated IRL after meeting during the series.
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Rebel Without A Cause
Jim Stark. Rebel Without a Cause: James Dean is practically the OG of all bad boys on-screen. With his star-making turn as Jim Stark, he broke hearts of girls across the world (and encapsulated most parents’ fears).
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Toxic Waste Benefit at MGM
Billy Hicks, St. Elmo’s Fire: Rob Lowe’s unbelievably good-looking Billy was the crown jewel of the Brat Pack’s most infamous movie. Flanked by a young Demi Moore and Judd Nelson, Lowe was the epitome of reckless youth as a saxophone-playing deadbeat father and husband who leveraged his good looks against his bad behavior.
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Patrick Verona, 10 Things I Hate About You: Heath Ledger’s Patrick Verona was a high school derelict with a heart of gold — and the only one who could tame (and win the heart of) shrewish Kat.
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“The Basketball Diaries” Premiere – Westwood, California
Jim Carroll, The Basketball Diaries: While some might argue that Leonardo DiCaprio’s turn in Catch Me If You Can or any of his Scorsese films might be more badass, his edgy role as an up-and-coming basketball star turned drug addict living hard in downtown New York marked a turning point in his career.
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“Reefer Madness” – Showtime’s New York Premiere
Logan Echolls, Veronica Mars: Anyone who’s watched Veronica Mars knows that Kristen Bell does not need the drama of her on-again, off-again relationship with Logan (played by Jason Dohring), which is further complicated by the fact that he used to date her bestie, Lilly, who was murdered at the beginning of the series. But their snarky, steamy chemistry is hard to beat — we definitely don’t blame Veronica for coming back for more.
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Amnesty International Event – 1988
Bender, The Breakfast Club: Judd Nelson’s Bender might be the penultimate pop culture bad boy. Coming from a troubled home and termed a “criminal” in the famous letter penned by Michael Anthony Hall in the movie, he not only got the girl but did it while in detention.
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Celebrity Sightings In Los Angeles – April 26, 2010
Mark “McSteamy” Sloan, Grey’s Anatomy: While everyone else was losing their shit over McDreamy, McSteamy was the one who caught our eyes. His bad boy credentials firmly in place (after all, he’s a plastic surgeon, not a virtuous neurosurgeon like Derek AND he had an affair with his best friend’s wife), Eric Dane couldn’t help but win us over with his Lexi storyline and big heart.
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Han Solo, Star Wars: Princess Leia might like nice men, but even she couldn’t help falling for a scoundrel (not a difficult feat when said scoundrel is a young Harrison Ford).
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The Lucky Magazine Club 2006 – Day 1
Tim Riggins, Friday Night Lights: The bad boy football player of Dillon High School pulled at our heartstrings when he supported Jason after his accident; the fact that Taylor Kitsch is pretty easy on the eyes helped warm our hearts to this Texas rebel.
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Lost Premiere On The Beach
James “Sawyer” Ford, Lost: Despite the ever-twisting plotlines of Lost, we found that we kept getting distracted by the island’s resident bad boy Sawyer (played by a rugged Josh Holloway).
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Premiere Of Relativity Media’s “Romeo & Juliet” – Arrivals
Chuck Bass, Gossip Girl: Ed Westwick’s Chuck Bass started out as the villain of the Upper East Side and progressed to becoming the king of the Empire Hotel (and Blair Waldorf’s heart), all while charming us with his debaucherous antics.
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Sarah Michelle Gellar And David Boreanaz
Angel, Buffy the Vampire Slayer: David Boreanaz’s Angel is probably the hottest undead we’ve ever seen. His dark and tortured past (oh, and the fact that he’s a vampire) only adds some heat to his romantic storyline with Buffy, whose destiny is to kill his kind.
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Reese Witherspoon And Ryan Phillippe At The New York Premiere Of Cruel Intentio
Sebastian Valmont, Cruel Intentions: Ryan Phillipe’s Sebastian was cruel, calculating, and very, very cute. It’s no wonder that former wife Reese Witherspoon fell for him IRL on the set of the film.
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Sauza Tequila Party Hosted by Jeremy Piven, Featuring the “Hug It Out” Margarita – Red Carpet and Inside
Kevin Volchok, The O.C.: Cam Gigandet’s Volchok was the ultimate surfer dude, but his ego and personal problems soon led to him becoming one of the most sinister figures on the show, eventually leading to the show’s apex of drama, when he kills Marissa Cooper in a bout of jealousy-fueled drunk driving.
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Peter Carrette Archive Collection
Dylan McKay, 90210: Luke Perry as Dylan McKay was so smooth that one of our editors said she would be tempted to cough up $1200 for the Vetements sweatshirt printed with his notorious line, “May the bridges I burn light the way.”
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Cry-Baby Premiere
Wade “Cry-Baby” Walker, Cry-Baby: Johnny Depp as Cry-Baby, the handsome leader of a band of rogue misfits was charming enough to woo the preppiest do-good girl in town into heading to the wrong side of the tracks and honestly, we can’t blame her. Swoon.
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Balthazar Getty And Spotify Present A Night With PurpleHaus Music
Jesse Pinkman, Breaking Bad: Aaron Paul’s Jesse Pinkman is the cutest meth-making outlaw we’ve ever seen — sorry, Walter White.
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Mad Max: Fury Road Photocall – The 68th Annual Cannes Film Festival
Tony Stonem, Skins (UK): When you see Nicholas Hoult as Skins’ narcissistic cad and shameless playboy, it’s hard to remember that he was once the boy in About a Boy. Stonem’s hard-partying ways and promiscuity showed that it was definitely fast times at Roundview College.
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Actor River Phoenix Portrait Session
Chris Chambers, Stand By Me: River Phoenix’s wild child ways in Stand By Me eerily mirrored his own rebelliously youthful life (and sadly tragic end.)
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Mr. Big, Sex and the City: Mr. Big might be pop culture’s most polarizing romantic figure. No Mr. Darcy, he epitomized the man you knew was bad news, but you couldn’t stay away from. Chris Noth’s suave bravado as the dapper Mr. Big fueled the big city dreams of millions of girls who dreamed of Carrie’s highly unrealistic life in the Big Apple.
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The 54th Annual Golden Apple Awards
Daniel Cleaver, Bridget Jones’ Diary: Bridget’s boss slash two-timing boyfriend, Daniel Cleaver, proved that despite common sense and easy access to a nice man like Mark Darcy, one is not always immune to the charms of a ladies’ man.