Ranking Dylan McKay’s Top 5 Girlfriends on 90210 [VIDEO]

While their affection for each other was little more than a 'flash in the pan', Emily Valentine's prowess was strong enough to divide Dylan and BFF Brandon Walsh for a short time in high school. Plus, all the girls vilified her and labeled her 'trouble'.

Played by: Christine Elise

Valerie swept into town as a Walsh Family friend, occupying Brenda's old bedroom, and eventually the bed of her boyfriend Dylan! While she played good girl by day, Valerie was alllllll bad influence by night, especially when she crossed paths with Dylan. But they were worthy adversaries to say the least.

Played by: Tiffani-Amber Thiessen

Brenda was Dylan's high school sweetheart, and they were all romance and, sometimes, angst. Brenda lost her V-card to McKay, and even tried to run away to Mexico with him. But whilst on a semester in Paris, Dylan committed the ultimate sin -- falling in love with her best friend.

Played by: Shannen Doherty

Enter Kelly Taylor. Kelly was Brenda's best friend, and while summering at the Beverly Hills Beach Club, began a fling with Dylan that turned red-hot, serious romance. Kelly and Dylan would later discover that they were SO deeply connected, that they may have loved each other in a past life.

Played by: Jennie Garth

Toni is tops because she's the only girl Dylan McKay actually MARRIED. They're love was short but intense, and hated by her father. Toni became the subject of a hit-gone-wrong in which her dad tried to have Dylan killed. But she became the unintended victim, getting shot to death while driving Dylan's Jag. It's still one of the most heartwrenching scenes in 90210 history when Dylan gets to her too late and she falls out of the car lifeless.

Played by: Rebecca Gayheart