Grandma's Boy (2006) 
A Recipe for Success
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1 - middle aged man who hasn’t really grown up yet
Several - zany friends who look to the main character as their leader
1 - hot blond who is grown up but finds herself attracted to childish 30 something with potential
1 - nice old lady who wows us with her coolness
1 - crazy guy who is in competition with the main character
Garnish with several SNL veterans sprinkled in roles throughout
Directions: Provide impetuous for main character to get his act together in some way. Love interest aids him in getting act together and falls in love with him along the way. Throw in some funny stuff along the way and you have a Gilmore/Madison production.
As canned as this setup is, it still works for me. Why mess with a good formula? I was pleasantly surprised by this movie. I thought the zany side characters were all in nice doses and there were a couple of really good scenes, mostly involving the best friend. A lot of the gags are just telegaphed way ahead of time, but maybe this is just comedic foreshadowing? Most of the enjoyment stemmed from how nerdy all of the videogame people were and I guess that was enough to carry the film.
