Rachael Leigh Cook has been linked to many high-profile celebrities throughout her career, especially when she was a rising star in the '90s. The actress made a name for herself in Hollywood with her 1995 debut as Mary Anne in The Baby-Sitters Club. She went on to play Becky Thatcher in Tom and Huck before landing the role of Laney Boggs in 1999's She's All That. As her career skyrocketed to the top, Cook became a magnet for equally as successful men in the entertainment industry. Her former flames include Shane West, Rider Strong and Ryan Reynolds.