Catherine Zeta-Jones and Michael Douglas
Credit: Amy Graves/WireImage, Kevin Mazur/VF13/WireImage, Tony Barson Archive/WireImage

When news broke that Catherine Zeta-Jones and Michael Douglas, one of Hollywood's longest-standing couples, are "taking a break" after 13 years of marriage, we were heartbroken. It’s no secret that the duo had fallen on dark times as of late, given Douglas’s 2010 battle with cancer and Zeta-Jones's struggle with bipolar II disorder, which she made public in 2011. In the December 2012 issue of InStyle, Zeta-Jones talked about her marriage: "It's been an intense time, in good ways and bad. You find out who you really are and who you're married to. You find things inside yourself you never imagined were there." Looking at these red carpet moments from years past, we never would have imagined these two were headed for a split. See their top red carpet moments.