5. Brett Favre in There's Something About Mary
But, what about Brett Fav...rah? Actually, that's the most memorable part of Brett Favre's cameo in this movie, and he wasn't even in the scene. Still, athlete cameos are a common occurrences, so I felt they needed to be addressed here. They're usually horribly stilted and unintentionally hilarious, and this is no exception. Watch Favre while he's in a shot and not giving dialogue. Dude is terrified. It's awesome. The choice came down to him and Lance Armstrong in Dodgeball.
4 (tie). Ben Affleck and Matt Damon in Jay and Silent Bob Strike Back
I could probably do a whole top five just using Kevin Smith movies. Hell, maybe five just in this movie alone. The cameos in Jay and Silent Bob are on the bubble, teetering between fun and tiresome. They're too knowing, but... Good Will Hunting 2: Hunting Season? Hilarious. Affleck's hookers? Perfect. Too bad the dude kept making crap movies after this, kinda negating any good will he may have earned by acknowledging the crap that was Forces of Nature or Reindeer Games.
3. Topher Grace in Ocean's Eleven
Like Matt and Ben's cameos above, Topher had no problem making himself look like a movie star cliche, only in Ocean's he played it straight (whereas Matt and Ben LITERALLY played to the camera). The result is a much better, and much more memorable cameo. Easily one of the highlights of a great movie.
2. Neil Patrick Harris in Harold & Kumar Go to White Castle
How good was Harris in Harold & Kumar? So good, that his turn as a drug-fueled poonhound basically reshaped his career from child star has-been to inform his performance in How I Met Your Mother. The part wasn't written for him, but basically, Barney Stinson is a network-friendly version of his "Neil Patrick Harris" in this. The only quibble with his placement is that he's the fourth-listed actor on the credits of the movie, so it's not really a cameo. But the important part of this list is "celebrity as themselves", not "cameo".
1. Bob Barker in Happy Gilmore
Here it is, my motivation for this list. Bob Barker's last Price is Right airs tomorrow, and I wanted to pay tribute to the man who entertained me every summer when I was out of school, watching daytime TV. I really hope that they don't replace him. Just let the show finish, and live forever in syndication. Not that it matters, I'd never watch a non-Bob Price is Right anyway. Could you imagine what it would be like to be his replacement, then have to take a putt for the first time? BUCKETS of sweat. Worse than trying to win the Masters.
I wonder how many times Bob had to deal with jokers saying "the price is wrong, bitch" to him on air after this movie, then the show having to cut and reshoot the sequence. I bet he slapped a bitch every now and then. Still, it was so worth it. All celebrity cameos will be judged based on this. Forever.