Van was born in Toronto, Ontario, and dropped out of Bloor Collegiate Institute in Grade 11 to pursue a career as an entertainer.

[2] The single "I Miss You" / "The Last Sunrise" by the Billy Van Four, released on the Rodeo International label, peaked at number 29 on the CHUM Chart in Toronto in March 1961.

[3][4] As a comedian, Van gained national attention in 1963 as a performer on CBC Television's late-night satire programme Nightcap.

Van appeared in a six-part spinoff series, Flemingdon Park, based on a recurring Nightcap skit, that aired at the beginning of 1967.

[7] The characters included the Count (Count Frightenstein, for which he put on a fake Bela Lugosi-type voice); Grizelda the Ghastly Gourmet (an old witch with a cauldron who did a cooking show); the Wolfman, who, in an imitation of DJ Wolfman Jack would play records, and dance to them, while wearing a werewolf costume (rock songs from Sly and the Family Stone, The Archies, or other bands of the era were played in their entirety); the Librarian, an ancient bearded character who tried "to horrify you" with benign fairy tales from dusty old cobwebbed volumes, then would be disappointed when the unseen viewers were not horrified; Dr. Petvet, who would bring animals onto a set and talk about them (his catchphrase was "Pets are friends"); and the Oracle, who would give astrological readings, and answer fake letters from viewers while wearing a large headdress and speaking in a Peter Lorre voice.

Second Banana is also an historical look at life in Toronto in the 40's and 50's and the infancy of Canadian television; a behind-the-scenes insight from a performer's perspective and reveals the often not-so-glamorous side of being an entertainer.