What's especially impressive is that the previous record-holder had held the top spot for almost 25 years: It was Beverly Hills Cop. That film made $234,760,478 back in 1984 and '85, and for a quarter-century no R-rated comedy could top it. The closest anything came was Wedding Crashers, which made $209.3 million in 2005.
The Hangover, directed by Todd Phillips, is #3 among R-rated movies of all genres, behind Passion of the Christ and The Matrix Reloaded, neither of which are comedies, at least strictly speaking. It would have to make another $46 million to surpass Matrix Reloaded, and that probably isn't in the cards, so it will have to content itself with being #1 in the R-rated comedy department. It will probably hold that record for a while, too -- of the top 20 R-rated movies of all time, only six are comedies. Strangely, none of them have Judd Apatow's name attached, either. Can we start a feud between Phillips and Apatow?
If you're wondering how The Hangover stands among comedies of all ratings, forget about it. About a dozen G- and PG-rated animated comedies have made more money, not to mention live-action comedies like Night at the Museum and Home Alone. The R-rated comedy is a genre unto itself, and that's where The Hangover reigns supreme.