Val Kilmer has dated his fair share of Hollywood legends, but his breakup with Daryl Hannah stung the most. “Lord knows I’ve suffered heartache. But Daryl was by far the most painful of all ...

Daryl Hannah & Val Kilmer during "Wonderland" Premiere hosted by DETAILS + GUESS? - Arrivals at Grauman's Chinese Theatre in Hollywood, California, United States. Gregg DeGuire/Getty Images ...

He’s dated Cindy Crawford, Angelina Jolie and Cher, but Val Kilmer says his breakup from Daryl Hannah was by far the most difficult. Hannah, 59, and Kilmer dated in 2001 after working together ...

Val Kilmer enjoyed romances with the likes of Cher, Angelina Jolie, and Cindy Crawford, but he said his split from actress Daryl Hannah was the most painful of all.

Val Kilmer arrives at the Warner Bros. premiere of "Kiss Kiss Bang Bang" held at the Grauman Chinese Theater on Oct. 18, 2005, in Hollywood, California. Daryl Hannah is his biggest romantic regret ...

Val Kilmer was linked to Cindy Crawford, Angelina Jolie, ... While he moved on from his spouse with Crawford in the '90s, he referred to his split from Daryl Hannah, ...