One crucial element of classic Adam Sandler comedies is the antagonist.  The Sandman created a genre in which the villain provided tremendous comedic fodder.  The bad guys countered his slacker characters’ relatable charm with the despicable trappings of snobby rich guy society.  Here are the most memorable:

5. Chuck Cedar – Mr. Deeds

Sandy Cohen as a bad guy?  Seems unfathomable.  But the year before Peter Gallagher took the role of superdad on The O.C., he played scheming Blake Media executive Chuck Cedar.  Cedar was hellbent on stealing control of the conglomerate from small town dimwit Longfellow Deeds (Sandler), who inherited billions when his great uncle Preston Blake froze to death atop Mt. Everest. Cedar takes the Blake chopper to New Hampshire to meet Deeds and – judging him as a simpleton – thinks he’s got it made in the shade.  Deeds antics in New York City turn Cedar’s takeover plan on its ear; so he has to resort to even more devious tactics.  He conspires with an Inside Edition-type show runner to break Deeds’ heart and send him running back to New Hampshire.  However, the previously emotionless Babe Bennett (Winona Ryder) falls for Deeds while deceiving him as part of the evil plot.  She redeems herself by discovering the true heir to the Blake fortune is Emilio Lopez (John Turturro), Preston’s love child.  Cedar is defeated and run out of the shareholders’ meeting on a rail.

4. Glen Guglia – The Wedding Singer

Glenn is the ultimate 1980s douchebag.  He keeps Julia (Drew Barrymore) at an arm’s length while he’s busy chasing tail all over the clubs.  He’s more interested in shooting Alabama Slammers and emulating Don Johnson than he is in participating in wedding planning.  His cronies take him out for a bachelor party, which ends in an altercation with Robbie (Sandler), the good-hearted title character.  Glenn believes his financial sector career makes him impervious to competition from any man below his tax bracket.  That is, until Billy Idol locks him in an airplane bathroom while Robbie sings Julia a love song he wrote especially for her.  Julia picks Robbie to grow old with, despite her vision of Glenn someday resembling Blake Carrington.

3. Bob Barker

It’s one of the great fight scenes in Adam Sandler film history.  The whole sequence builds up the tension and it culminates in a masterfully choreographed fist fight.  The game show host really shows off his acting chops, as he genuinely seems pissed off at Happy’s hack round. Barker punctuates the KO with the final word: Bitch.

2. Shooter McGavin

Joe Flaherty’s heckler who irked Happy before his duel with Barker was hired by the film’s true villain: Shooter McGavin.  Shooter easily earns consideration for 90s comedy nemesis Mount Rushmore alongside Big Ern McCracken and 2 Rob Lowes (Wayne’s World and Tommy Boy.)  Shooter is visibly perturbed when Julie Bowen touches his clothes, not long after he instructed her to get him a Diet Pepsi. He uses a canned David Hasselhoff/sand joke more than once. Shooter’s proneness for being outwitted in arguments with Happy steam his brain, leaving him unable to come up with anything but a loud “NO” when asked if he eats pieces of shit for breakfast.

Shooter is insecure about his lack of a winner’s jacket and he’s not about to let some “freak, sideshow” steal his moment in the sun.  Shooter McGavin’s story ends with an unseen ass-beating at the hands of Happy’s former construction boss, the gigantic Mr. Larsen.  Mr. Larsen leads the chase after Happy’s trick shot wins the tournament and Shooter attempts to run off with the gold jacket.  The audience does get to hear the pounding happen as the scene fades.

1.  Eric Gordon – Billy Madison

Eric desperately wants to manage the Madison Hotels chain when Mr. Madison (Darren McGavin) retires.  The man with the weasel laugh is willing to go to great lengths to prevent the rightful heir – drunken buffoon Billy Madison – from taking the reins.  Billy proposes re-entering school and completing each grade to prove he’s not an idiot.  When Billy starts succeeding, Eric can’t even have fun at the graduation parties.  He begins countermeasures.  He blackmails the elementary school principal, turns the janitor into a spy and eventually wields a gun.  Unable to answer a business ethics question during the ultimate 1-on-1 Eric vs. Billy academic decathlon to determine the future CEO of Madison Hotels; he points a revolver at Billy’s beloved Veronica Vaughn.  Luckily, Steve Buscemi intervenes, shooting Eric in the butt cheek with a rifle.   Bradley Whitford would go on to more applauded and serious roles, but I’ll always remember him as Billy Madison’s arch rival.