Demi Moore & Ashton Kutcher
Demi and Ashton have to be one of the most iconic couples in Hollywood history. Yes, we know Ashton is happily married to former costar Mila now, but we have to relive this for just a second. So, the couple that had 16 years between them, married in 2005. For years they were the talk of the town, but it rarely seemed to affect them. Sadly, in 2013 the couple separated. Now, as we mentioned, Ashton has a child with his wife Mila Kunis.
Katie Holmes & Tom Cruise
Again, this couple was a Hollywood staple despite the 16 year age gap. Katie and Tom tied the knot in 2006, but had been dating for 7 years prior. Together they had daughter Suri, but sadly divorced in 2012.