Flanagan was born in Perth Amboy, New Jersey, grew up in nearby Highlands and attended Henry Hudson Regional High School with Smith.

He also designed the clown animation that made up the View Askew logo, and appeared in the Soul Asylum video for "Can't Even Tell", directed by Kevin Smith.

Flanagan and Johnson reappear as Walt Grover the Fanboy and Steve-Dave in a deleted scene in Smith's 1997 romantic drama Chasing Amy.

[4] In 2007 the two collaborated on War of the Undead, a miniseries set in 1945 in which the Third Reich hatches an ill-fated plan to employ Count Dracula, the Wolfman and Frankenstein's monster as weapons in a last-ditch effort to defeat the Allies.

The series featured the villains Onomatopoeia (a character created by Smith during his run at Green Arrow), The Joker, Maxie Zeus, and Victor Zsasz.

[8][9] After issue six was published, Smith and Flanagan's work on their reality show, Comic Book Men, extended this planned break further than expected.

Fellow co-host Bryan Johnson is the author, with Ming Chen and Mike Zapcic helping with character creation.