Owen & Woody: A Fine Bromance
Longtime pals Harrelson, 48, and Wilson, 40, play a round of golf while vacationing in one of their favorite spots – Maui, Hawaii – on Sept. 22. "I was scheduled to stay four days, and I stayed four weeks," Wilson tells PEOPLE of crashing with Harrelson's family. "By the end, his wife was like, 'Hey, do you need a ride to the airport today?' "
While vacationing in Portofino, Italy, Harrelson and Wilson try to lay claim to a water toy – by wrestling for it! – on July 18. The duo eventually gave their spirited high-seas hijinks a rest, relaxing in the sun on a yacht.
DINNER À DEUX
Later that evening, the actors share a laugh on steadier ground while indulging in Italian cuisine at ISEO restaurant in Portofino.
GAME, SET, MATCH!
Taking a break from filming Marley amp Me in Florida, Wilson joins Harrelson in the front row to watch a Serena Williams match at the Sony Ericsson Open in Key Biscayne on April 5, 2008. After the game, the stars reportedly skinny-dip outside of Harrelson's beachfront home.
NEW YEAR'S TOAST
In January 2008, Wilson and Harrelson drink in the Zombieland star's last months as a bachelor after a swim in Maui. Later that year, Harrelson wed his longtime girlfriend Laura Louie on the Hawaiian island.
LENDING A HAND
On the mend from his attempted suicide, Wilson takes a guys' getaway with Harrelson in Cusco, Peru, in December 2007. During their weeklong stay, the duo swam in ditches and visited a children's home that Harrelson supports. "He wants his privacy now," Harrelson said of his pal at the time. "He's doing incredibly."