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.

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 ...

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 ...

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 ...

However, one woman left a significant mark on him. Val was involved with actress Daryl Hannah after they met on the set of In God We Trust in 2001.

Daryl Hannah is his biggest romantic regret Kilmer writes rapturously of his romances – and there were many. He was "hopelessly in love" with Carly Simon.