25. Conan O’Brien & Jeff Garlin

Conan O’Brien is one of Hollywood’s most distinguished talk show hosts. He was the host of the Late-Night talk show from 1995 – 2009, spanning an impressive 2,725 episodes. He is held to such a degree of esteem that we usually forget that he was once an aspiring comedian himself.

Interestingly, during his trying days as an aspiring comedian, he lived in an apartment in Chicago and had Jeff Garlin as his roommate during the late 1980s. Jeff, of course, is also a distinguished Hollywood comedian known for his roles in sitcoms such as Arrested Development and Curb Your Enthusiasm. Together, Jeff and Conan in the apartment across Wrigley Field dreamt of making it big in the Hollywood industry. Moreover, the two of them would even hone their comedic prowess together, writing skits and practicing impressions for their own amusements.