Hmmm...Parachute Pants region, first round:
Breakfast Club v. Bill & Ted's Excellent Adventure -- Despite its notoreity, I have only seen the Breakfast Cllub once and di not take much from it. That said, when matched with one of the stupidest movies of the decade, come on. Bill & Ted weren't even that funny, and were upstagfed a few years later by Beavis & Butthead. Has to be Breakfast Club. As an aside, forgot whether Keanu was Bill or Ted, but how would you like to be the OTHER guy in Bill and Ted and watch your partner in stupidity go on to megastardom while you are forgotten? breakfast Club.
Midnight Run v. Say Anything -- I am aware of Say ANything as a John Cusack movie, but have never seen it. Was nto even until the latre 90s that I first became ware that John Cusack was a major player in the chick flick market. In any case, I considered Midnight run cosniderably overrated, and thought Grodin was funnier in Taking Care of Business (across from the less talented Belushi brother), but since I can't say I've even seent eh toeh and anticipate major cheese...Midnight Run.
Naked Gun v. Brewster's Millions -- Anybody rooting for Brewster's Millions in this matchup needs to be taken outside and given the OJ treatment. Naked Gun is a top 10 all time funny movie and should be a serious threat to make it out of this bracket. Richard Pryor was last funny int he late 1970s while high on cocaine and cussing up a storm. Naked Gun.
48 Hours & Cocktail -- another are you kidding matchup, 48 Hours might have been a little overrated, but not THAT overrated. Also pretty sure that was my first unaccompanied by adults R rated movie.

48 Hours.
Revenge of the Nerds v. Red Dawn -- don't ever go back to Revenge fo the NErds -- ti was just not that funny, and juvenile. Of course the same could no doubt be said about the wonderful Cold War paranoia of red Dawn (and I think it was like the Mexicans or Nicaraguans or somebody who actually somehow invaded us there and we could not expel them -- er...right). But going with Dawn for some wonderfully paranoid cheese. Red Dawn.
Sixteen Candles v. Stripes -- with all apologies to the very pretty Molly Ringwald, Bill Murray, Harold Ramis, John Larroquette, Judge Reinhold, Joh Candy etc...Stripes.
Footlosse v. Lethal Weapon-- Footloose was actually a surprisingly good movie when I finally saw it. you make a movie centered around dancing set in some hick town and I epxected disaster. But there was some real attempt at telling a story there. However Lethal Weapon rocked, and for a long time was my favorite pure shoot 'em up action flick. Also you had Mel playing as it turned out himself -- a nut. But a badass nut. Glover's daughter was very cute too. Lethal Weapon.
Wall Street v. Pretty in Pink-- well..hate to knock out both Ringwalds, and if this had been Sixteen Candles maybe go I the other way but anyway... I did not love Wall Street, and have known enough people on Wall Street to put the Hollywood to it, but still Oscar winner etc. vs. a second rater. Wall Street.