Oh, Jess. The quintessential high school bad boy who stole Rory from Dean while simultaneously stealing our hearts. Jess is your standard kid from the wrong side of the tracks, whose background toughened him up and gave him his signature sarcasm. Enter Gilmore Girls sweetheart, Rory Gilmore, the nicest and most innocent person on the planet. Sparks fly, drama ensues, and we loved every single minute of it.
Best bad-boy line: "I wanna be good. Life's just not letting me."