This is David Cross in his HBO special, The Pride is Back. Perhaps you know him from Mr. Show, or Arrested Development. Or Waiting for Guffman, or Space Ghost. He gets around.
He was a first investor in Kickstarter. Went to Emerson College in Boston, too.
Here he is in Seattle doing stand-up, which is how he got his start.
Strong Warnings for language and adult topics, and humor. You may be offended, cringe, and/or laugh.