1. James Woods and Ashley Madison - 39 Years
James Woods is notorious in Hollywood for dating much younger women. However, this new relationship really takes the cake. James is nearly three times the age of his young lady love Ashley and neither seems to mind at all. The two reportedly met through her father who just happens to be one of James' golfing companions.
2. Catherine Zeta-Jones and Michael Douglas - 25 Years
With a big age difference, Catherine and Michael still manage to make it work out. The super skinny actress and her husband Michael share a home and two children together, Dylan and Carys. While they also share the same birthday - September 25, they most certainly are years apart.
3. Harrison Ford and Calista Flockhart - 22 Years
Harrison Ford and Calista Flockhart began dating in 2002, married in 2010, and they're even raising her adopted son Liam together. His ex-wife Melissa Mathison was said to have scored $85 million in their divorce. He probably should have considered a pre-nup.
4. Demi Moore and Ashton Kutcher - 15 Years
Age is nothing but a number for Demi Moore and Ashton Kutcher. The two clicked over dinner in May of 2003, and have been going strong ever since. They were married in September 2005 and are raising Demi and ex-hubby Bruce Willis' three daughters together.
5. Billy Joel and Katie Lee Joel - 32 Years
Many doubted that the legendary singer Billy Joel and a much younger Katie Lee would make it past the first few dates. The critics were wrong and the two were married in 2004. He was 55 and she was 23 when they tied the knot at their home in Oyster Bay, NY.
Update: In June 2009, Billy and Katie called it quits.