Ex-Boyfriend by Lil Dicky (2013)

Dave Burd was an advertising account man in San Francisco when he spent two years making a rap mixtape on the side, which is the most San Francisco sentence on this list. Ex-Boyfriend was its first video, released on 23 April 2013, and it is a horror story: the narrator meets his girlfriend's former lover, discovers he is handsome, charming and, in the locker room, enormous, and spends the remaining verses doing the arithmetic on his own relationship. Every joke is a man measuring himself against a dick that has already left the building.

The video, directed by Brian Storm, passed a million YouTube views in its first twenty-four hours and has gone past thirty million since. It got Burd a career: the Professional Rapper album in 2015, the Freaky Friday single with Chris Brown in 2018, and Dave, the FXX series that gives an entire episode to the anatomy behind his stage name, which may be the most expensive piece of self-deprecation in television.

The afterlife is the stage name. Lil Dicky is the only artist on this list whose billing says the word, and Ex-Boyfriend is where he explains it. It is the purest size-anxiety record of the streaming era: no metaphor, no boast, just a man in a towel realising he has been graded on a curve and did not study.