What begins as a joyride in the Planet Express ship by Fry and Bender leads to the duo losing their jobs along with Leela, only to get new jobs working at Applied Cryonics. It's here where Fry meets his girlfriend from the year 2000 named Michelle, who is voiced by the delightful Sarah Silverman. And despite a painful guest appearance from Pauly Shore, "The Cryonic Woman" is able to become a hilarious Fry-centric episode. Michelle's inability to fit into the future is a perfect contrast to Fry, who didn't fit into the year 2000 and is truly at home in the year 3000. Oh, and don't forget that Michelle is also demanding and extremely selfish, forcing Fry into what he believes is the year 4000. This turn into a villain works exceptionally well, showcasing the struggle of finding a place where you belong.
45. I, Roommate
In a lot of ways, "I, Roommate" is the ultimate Fry and Bender episode, as it serves to crystallize the unique relationship between the two of them. It's an oddly moving episode that deals with the idea of friendship, a look at how the most compassionate bonds are the ones forged in fire. Fry's discomfort in his living arrangements with Bender is outweighed by the strength of their friendship, a simple statement of brotherhood that the show would lean on in the future between them. After all, sometimes all you need is a good friend and a comfortable place to be happy.