17. Jess (Gilmore Girls)
The second of Rory's three boyfriends on the series, Jess certainly provided the most source of drama. Not meekly pathetic like Dean, and not spoiled douchey like Logan, Jess managed to be compelling by playing the James Dean bad-boy angle. With his leather jacket and disdain for authority, Jess managed to briefly capture Rory's heart. Though the two separate, Rory bumps into Jess again during her college years. During their separation, he'd gone off on his own and matured some. He'd even written a short novel. Jess would be a great character to have been able to follow as he matured from a rebellious punk to an intelligent and artful man who was able to take care of himself. Also, any opportunity for Alexis Bledel to guest star in something works great for me.