Jake Gyllenhaal [1] has won over plenty of fans throughout the years. While he may have kicked off his career as a child actor in films like City Slickers and A Dangerous Woman, it wasn't until he broke back into the Hollywood scene as a young adult starring in movies like Donnie Darko [2] and Bubble Boy that people started noticing he was just as hot as he was talented. Some could argue that he has gotten better looking with age [3], but we can't seem to forget how adorable he was at the start of his adult acting career. So we rounded up 25 photos of the Hollywood A-lister from back in the day. Please enjoy.