Back in 1999, Gabrielle Union and — at the time — a lesser-known Heath Ledger starred in one of my favourite movies of all time, 10 Things I Hate About You. In it, Ledger plays the high school's resident bad boy, with long curly black hair and fitted T-shirts. Union, meanwhile, plays the ditzy, fashionable freshman who cares more about her popularity status than anyone around her. Off-screen, things were much different, Union says while appearing on Bravo's Watch What Happens Live. Ledger was a just a "doll baby" with "wild hair." She says the first time she met him "no one had ever really heard of him but he was this mysterious 19-year-old. He told me and anyone else who was over 21 to go meet him at the top of the hotel at this bar and we walk in and he's just got this wild hair. Again, he's 19 but he's got like a dad drink and he gets up, and he was such a man and such a gentleman, and his girlfriend at the time was like 38. He was a great, warm, funny...we had a lot of fun." She goes on to say that she thought all filming experiences were supposed to be like that: one big happy family. If you're in the mood to cry even more, then revisit this heartbreaking interview where Jake Gyllenhaal talks about his time with the late Ledger. Grab the tissues, and watch the clip below.