I have begun to like Steve Coogan in a few roles (he's barely in Tropic Thunder) and he tries very hard to make this part funny. One of the problems is that I never really believed that Coogan is a fool. Other Brit actors like Hugh Laurie and Rowan Atkinson can play the fool or the smartest guy in the room equally effectively, but Coogan never quite achieves the "talentless AND foolish" perfection.
Co-writer-director Andrew Fleming (Dick and The In-Laws remake) throws everything at the wall to try and make some jokes stick: there's a wise thespian voice-over, there's chapter title cards (like in Clerks), there's recurring physical comedy (Coogan rides rollerskates to work), funny costumes (Coogan wears a caftan at one point), but half the jokes fall flat. The musical-within-the-movie is great: Hamlet and Jesus Christ go back in a time machine to save everyone who dies in Hamlet 1, including a slo-mo dash across stage to stop Queen Gertrude from drinking the poisoned wine. Hamlet and Laertes duel with lightsabers in midair, until they call a truce and start kissing. The music is a mix of Grease-style fluff ("Rock Me Sexy Jesus") and Rent-style sentimento-rock: the conclusion of the musical is set to the Gay Men's Choir of Tuscon singing "Someone Saved My Life Tonight." The original music was quite good but there wasn't enough of it.
Catherine Keener is starting to grate on me- she seems to have only one mode, and it's all too dull to cast her as the bitchy wife. It's a shame, because she was so subtle and sympathetic in The Forty-Year-Old Virgin. Inexplicably, David Arquette was cast in a part with only two lines: the lodger whom Keener runs away with. The adorable Melonie Diaz has become the mascot of underwhelming high-concept art-house comedies- she plays a student in Hamlet 2 and a girlfriend to Mos Def in Be Kind Rewind. Somewhat randomly, Elisabeth Shue plays herself as a Hollywood actress who got off the merry-go-round and became a nurse. When asked "what do you miss most about acting", she reminisces about how great it was to make out with her co-stars, which is funny by itself- how many times do we need to hear actors saying "love scenes are not fun"? But what takes the joke to a whole meta-level is that she ends the movie making big sloppy French kisses with Coogan- is she the only one who knows this is a movie?
There were also two appearances by classic "Hey it's that guy" veterans. Marshall Bell as the principal- I remember him best for having the Martian revolution leader growing out of his chest in Total Recall. He was Wil Wheaton's dad in Stand By Me and a crazy officer in Starship Troopers. Marco Rodríguez plays the father of one of the students. He hasn't had an iconic movie role, but he's been on every big TV drama of the last 25 years, including recurring characters on Hill Street Blues, Cagney & Lacey, Star Trek: The Next Generation, L.A. Law, Nash Bridges, NYPD Blue, JAG, CSI, and Cold Case.
Oh, I almost forgot the funniest moment in the movie- Coogan is planted in front of his keyboard trying to write his HAMLET 2 script. He has been at it for 46 hours straight. He is strung out, exhausted, wired, and desperate. His housecat is sitting on his computer printer, purring. Slowly he turns to the cat, and growls "What the f**k is YOUR problem?" (At the Landmark Embassy in Waltham with Amy)