3. Dress for Success. Fred Funk made his Skins Game debut in 2005. Funk, who is popular with crowds because he wears his emotions on his sleeve, turned into a Skins Game king. He won 15 of 18 skins and racked up a record haul of $925,000. But Funk's contribution to Skins Game history was more than his stellar golf. A short hitter, Funk had a bet with Annika Sorenstam that if she outdrove him on any hole, he'd put on a skirt.
When ABC reporter Andy North noted in the third fairway that Sorenstam had the edge, Funk pulled a flowery pink skirt out of his bag and put it on, leading to hysterics among the other players and gallery and ensuring his spot in Skins Game lore. The pinnacle moment came at the green when Tiger Woods slyly walked over to help Funk line up his putt. "What do you think, Tiger?" Funk asked. Woods, barely able to contain his laughter, answered, "Two balls out."