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One of my Flickchart philosophies is that there should be no “automatic” wins. Just because I call Lost in Translation my favorite movie doesn’t mean that the match-up shouldn’t warrant full consideration (in fact, I never would have realized that it was my favorite movie if not for this philosophy.) So let’s look at the opposition here. The 40-Year-Old Virgin is pretty much the cream of the crop of the Judd Apatow brand of comedy. It’s hilarious, the cast is hitting on all cylinders, and there’s real affection for the main character and his plight. I’d call it one of the finest laugh-out-loud comedies of the 2000s. There. Case made. Lost in Translation is still better. Its meditative nature and profound tale still strikes all the right chords for me, and it keeps growing all the more relevant to me for every year as I traverse the age gap between Charlotte and Bob.