• 10. Michael Douglas And Katherine Zeta Jones (25 Year Difference)

    10. Michael Douglas And Katherine Zeta Jones (25 Year Difference)

    The two married in 2000 when Zeta-Jones was 30 and Douglas was 55. And 11 years and two kids later, the pair is still going strong!

  • 9. Megan Fox And Brian Austin Green

    9. Megan Fox And Brian Austin Green

    Megan Fox married Brian Austin Green when she was just 18 years old.

  • 8.Tom Cruise And Katie Holmes

    8.Tom Cruise And Katie Holmes

    Tom Cruise And Katie Holmes may be 16 years apart, but the difference in age seems to work for them. Strange to think that when Katie was 3 years old, Tom was starring in his first film, Endless Love.

  • 7.Calista Flockhart And Harrison Ford (22 Year Difference)

    7.Calista Flockhart And Harrison Ford (22 Year Difference)

    Here’s a couple that seems to embrace the 22 year age difference well. Harry and Ally are still going strong!

  • 6. Soon-Yi Previn And Woody Allen (35 Year Difference)

    6. Soon-Yi Previn And Woody Allen (35 Year Difference)

    Although Woody Allen may have recently lost his title as king of the cradle robbers, it doesn’t make his 35 year age difference with wife, Soon-Yi any less strange. (And would you believe that’s not even the most bizarre thing about this couple.)

  • 5. Courtney Stodden And Doug Hutchison (35 Year Difference)

    5. Courtney Stodden And Doug Hutchison (35 Year Difference)

    Doug Hutchison recently stole the crown from Woody Allen when he married 16 year old Courtney Stodden. But hey, 35 years is just a number, and this is a love that will last forever.

  • 4. Alice Kim And Nicolas Cage - (20 Year Difference)

    4. Alice Kim And Nicolas Cage - (20 Year Difference)

    Despite a 20-year age difference, these two love birds seem to be doing just fine.

  • 3. Clint Eastwood And Dina Ruiz (36 Year Difference)

    3. Clint Eastwood And Dina Ruiz (36 Year Difference)

    After 15 years together, Clint and Dina seem to still be crazy in love.

  • 2. Rod Stewart And Penny Lancaster (26 Year Difference)

    2. Rod Stewart And Penny Lancaster (26 Year Difference)

    Despite a pretty hefty difference in age, as well as height, Rod seems to have found true love in his third marriage.

  • 1. Allen Gregory And His Principal (48 Year Difference)

    1. Allen Gregory And His Principal (48 Year Difference)

    Allen Gregory’s crush on his principal is no secret. And although these two may never actually be together, their 48 year age difference earns them the #1 spot on this list.