Let's look at the leader board:
Syriana (2005) -- FLOP
Good Night, and Good Luck. (2005) -- FLOP (but made some $$ because Clooney comp'ed em)
Ocean's Twelve (2004) -- FLOP (broke even=flop in Hwd)
Intolerable Cruelty (2003) -- MEGA-FLOP
Confessions of a Dangerous Mind (2002) -- FLOP
Solaris (2002) -- ISHTAR-LEVEL FLOP
Welcome to Collinwood (2002) -- FLOP!
So the last movie Loonie Cloonie was featured in that didn't die in the box office was Ocean's 11 -- and that was a boring and unecessary remake of an originally good movie by the Chairman Of The Board.
I didn't count Spy Kids -- he is a cameo.
That Gulf War movie he made was also horrible. The only movie he ever made that I liked was the one where he was an escaped convict in the 30s. He was in his element, playing a hillbilly.