I’d be hard-pressed to find an event as bizarre as Norman Mailer’s quixotic 1969 mayoral campaign in the annals of New York City political history. Running alongside newspaper writer Jimmy Breslin (who was running for city council president) under the slogan of “no more bullshit“, the Mailer-Breslin ticket sure seems a lot more interesting than the prospect of somebody running against, and getting whooped soundly by Michael Bloomberg.

I’d also be hard-pressed to try and find another personality quite like Mailer’s, and if you do a simple search on Youtube, you can find many examples of the late writers brilliant, somewhat insane legacy.

#1 Mailer vs. Rip Torn
Mailer made a series of experimental films in the late 1960’s, but I’m not sure if any of them are as infamous as Maidstone, which doesn’t only feature an appearance by Hervé Villechaize (Tattoo from Fantasy Island), but also this fight – acted or not – between Mailer and actor Rip Torn.

#2 Mailer vs. feminists
As documented by in the film Town Bloody Hall by D.A. Pennebaker, in 1971 Mailer went toe to toe with some feminists – including Germaine Greer – and of course, hilarity ensued.

#3 Mailer vs. The Gilmore Girls
Remember that time Mailer was on that WB show that I (secretly) really liked? Weird and awesome.

#4 Legos act out Mailer’s 1965 novel An American Dream, stupidity ensues.

#5 Norman Mailer becomes part of Brit Pop history
As if you didn’t need another reason to think Lloyd Cole was a genius, he rhymes “read Norman Mailer” with “or get a new tailor” on the 1984 song “Are You Ready to be Heartbroken?”