An unemployed cocaine addict named Dennis (Samberg) goes on drug binge while singing an elaborately choreographed Disneyesque musical-theater number about how it is going to be a great day. The more cocaine he snorts, the faster he sings, and the more disjointed and surreal the song becomes. Eventually the whole experience is revealed to be a vivid, cocaine-induced hallucination. 9th music video on Lonely Island's album, Turtleneck & Chain.

Saturday Night Live Backstage is a 2011 documentary comedy TV movie.

A handsome high school student obsessed with his good looks (Samberg, portraying Gene Hackman as the protagonist) is cursed by a witch (Nasim Pedrad), who transforms him into the same nerd that Samberg played in the previous Digital Short The Roommate. Having been informed by the witch that he has one year to find someone to love him "or stay like this forever", he falls in love with a girl (played by episode host Miley Cyrus) who seemingly attempts to find his inner beauty, albeit unsuccessfully.

The second consecutive Digital Short to parody a then-recent Hollywood release, it appears to be the origin story for The Roommate character, implying that he was unable to break the witch's curse.

Nasim wants to be inspired, so she finds Helen Mirren in her dressing room, where Pedrad dreams she is in "Helen Mirren's Titties", a place beyond space and time, and a sequence of shots involving happy things like two leaders shaking hands, flowers, etc.

At a clothing store, a man (Samberg) is unconvinced that the V-neck shirt he is trying on is for him, despite his girlfriend's (Pedrad) assurances. But when the store owner (episode host Ben Stiller), wearing a deeper V enters, Samberg attempts to one-up him and asks a clerk for "something deeper" starting an impromptu V-neck battle, ending with the store clerk getting arrested for indecent exposure.

In an early '80s-style instructional video, a nerdy man dressed like Carl Sagan (Samberg) shows viewers how to seduce women by playing chess, but the first two women (played by Nasim Pedrad and Abby Elliott) beat him. The instructor then changes the game to checkers and still gets beaten by a woman (Kristen Wiig). He tries Jenga, but ends up knocking the tower over. He tries eating glass, but ends up scaring the woman he's trying to seduce (played by special guest Olivia Wilde). The instructor (with his lips and mouth now bandaged up) gives up and lectures on how to hire a prostitute. The prostitute (played by episode host Jason Segel) offers sex to him for $5000, but the instructor only has $60. The instructor is stabbed and robbed of his money. Before dying, the prostitute comes back and beats him at chess.

Katy Perry and Samberg become best friends, then meet up with a "handsome drug addict" (Matt Damon) and "brilliant lunatic" (Val Kilmer) who want to be best friends too. Perry and Samberg become more and more frightened until Perry abandons the three when the drug addict shoots himself during a game of Russian roulette. The lunatic then builds a time machine, retrieving two cavemen, Marilyn Monroe (played by Nasim Pedrad), Amelia Earhart (played by Vanessa Bayer), Abraham Lincoln (played by John Solomon), and Julius Caesar from the past, who, along with Samberg, the lunatic, and the lunatic's "failed bird-man experiment" (who briefly left the duo to have sex with a white girl at the mall) wish the audience a merry Christmas and a Happy New Year.