[4] He variously wrote, directed, crewed, or starred in multiple theater productions including Macbeth,[5] The Lady's Not For Burning,[6] and Rashomon.

[7][4][8] He joined the Phi Theta Pi fraternity in 1958[5] became president of Alpha Psi Omega in 1960,[9] and won numerous awards and honors for art and theater.

[10][11][6] In 1961, he won second place in the President's Cup oratory contest for a speech in which he "suggested that pornographic or "sick" humor is gradually replacing clever satire.

[12][13] In 1985, 30 of his erotic illustrations were published in Personals: Only Real Men Need Reply by Glenlee Enterprises; a portion of all sales from the book were donated to charity for AIDS victims.

[20][21] Chuck Conner and Sean Platter cited Olaf as an inspiration for their 2008 comic series DEMONICSEX, which includes a foreward by Clive Barker.