Here is a list of good commencement speeches and funny films:
1. Will Ferrell's 2003 Harvard commencement speech. See if you can spot Al Franken in the audience.
2. Steve Jobs' 2005 commencement speech at Stanford University.
3. Ellen DeGeneres' 2009 commencement speech at Tulane University.
I was too lazy to add all the links, but you can find the speeches on YouTube.
Funny Films and Shows
1. The I.T. Crowd, Seasons 1 and 2
2. Adam's Apples, a Danish film
3. Wedding Crashers
4. My Cousin Vinny