Dumb and Dumber came out when I was a kid, but we've all probably seen it 20 times (not that we pass it up when it's on TV, though).
I think I saw Rounders years ago, but good suggestion, I'll probably watch it again.
We ended up watching Bottle Shock last night. A tiny bit drawn out at a couple parts, but overall we all enjoyed it:
In 1976, Steven Spurrier, a sommelier in Paris, comes to the Napa Valley to take the best he can find to Paris for a blind taste test against French wine. He meets Jim Barrett, whose Chateau Montelena is mortgaged to the hilt as Jim perfects his chardonnay. There's strain in Jim's relations with his hippie son Bo and his foreman Gustavo, a Mexican farmworker's son secretly making his own wine. Plus, there's Sam, a UC Davis graduate student and free spirit, mutually attracted to both Gustavo and Bo. As Spurrier organizes the "Judgment of Paris," Jim doesn't want to participate while Bo knows it's their only chance. Barrett's chardonnay has buttery notes and a Smithsonian finish.