Wedding Crashers (2005)

Keir O'Donnell plays artist Todd Cleary
Todd Cleary: “I made you a painting. I call it "Celebration." It's sexual and violent. I thought you might like it.”

Wedding Crashers on IMDB

'Bachelors and lifelong best friends, John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn) are business partners in divorce mediation in Washington D.C.. The friends frequently "crash" wedding parties to meet women, working from a set of rules taught to them by a past ‘crasher,’ Chazz. The duo always have cover stories for inquisitive guests and inevitably become the hit of every reception, to charm their way into bed with ladies at the wedding for a one night stand.

After a sequence of successful ‘crashes,’ Jeremy spots the wedding of the daughter of the Secretary of the Treasury William Cleary and his wife, Kathleen. After infiltrating the lavish event as brothers, John and Jeremy set their sights on two bridesmaids, also daughters of Secretary Cleary: Claire (Rachel McAdams) and Gloria Cleary (Isla Fisher). While Jeremy manages to make it on the beach with "stage-five clinger" and supposed virgin Gloria, John works on Claire. While talking afterwards, John is blocked by Claire's hotheaded and controlling Ivy League graduate boyfriend Sack, whom as the film progresses, isn't such a loyal boyfriend when he brags of his sexual conquests to his buddies behind Claire's back and seems to only want to marry Claire so he can advance his future political career by marrying into the family of powerful political figure. John convinces a resistant Jeremy to break the rules and accept an invitation to an extended weekend party at the Cleary family compound.

Jeremy and John are convinced into playing touch football where Jeremy is hurt by Claire's obnoxious boyfriend. Gloria puts Band-Aids on Jeremy, hoping to have sex with him. However, Jeremy turns her down with a philosophical love speech. Jeremy is shown to not really like Gloria all that much, at least not initially. At dinner later that day with Jeremy's assistance, John proceeds to spike Sack's wine with eye-drops which makes him sick, letting John have some alone time with Claire. That night, Gloria ties up Jeremy while he sleeps and then has her way with him. Jeremy is then visited by the girl's brother Todd later that night, thinking the two had "had a moment" earlier at the dinner table to which his advances are quickly rebuffed by a terrified Jeremy. '
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