His father, who was Estonian, escaped a concentration camp in Sweden after World War II by helping steal a minesweeper and sailing it to Ireland.

[7] Wool's combination of intelligent political comedy and burly Canadian demeanour has been described as "hoser savant.

"[14] Wool also hosted the 2016 show Before the Morning After, featuring comics filmed in a diner at the 2015 Edinburgh Fringe, for the NBC streaming service Seeso.

[9][15] Wool has toured the world extensively, telling one interviewer that he once circled the globe three times in two weeks, becoming so jet-lagged that he forgot what city he was in.

[22] He also voiced the character Hunter in the animated Disney XD short Lottie Bearshout: Good as Goaled, which won a BAFTA Children's Award in 2016.

Derek Riggs, who designed Iron Maiden's albums, did the cover for Wool's No Land's Man.