O'Donoghue's early career included work as a playwright and stage actor at the University of Rochester where he drifted in and out of school beginning in 1959.
During this period, he formed a group called Bread and Circuses specifically to perform his early plays which were of an experimental nature and often quite disturbing to the local audience.
Among these are an absurdist work exploring themes of sadism entitled "The Twilight Maelstrom of Cookie Lavagetto", a cycle of one-act plays called Le Theatre de Malaise and the 1964 dark satire The Death of JFK.
Drawn by Frank Springer, the comic detailed the adventures of debutante Phoebe Zeit-Geist as she was variously kidnapped and rescued by a series of bizarre Inuit, Nazis, Chinese foot fetishists, lesbian assassins and other characters.
Doonesbury comic-strip creator Garry Trudeau cited the strip as an early inspiration, saying, "[A] very heavy influence was a serial in the Sixties called 'Phoebe Zeitgeist'.
As one of many outstanding National Lampoon contributors, O'Donoghue created some of the distinctive black comedy which characterized the magazine's flavor for most of its first decade.
O'Donoghue appeared in the first show's opening sketch as an English-language teacher, instructing John Belushi to repeat the phrases, "I would like to feed your fingertips to the wolverines,", "We are out of badgers.
He later made appearances in the persona of a Vegas-style "impressionist" who would pay great praise to showbiz mainstays such as talk show host Mike Douglas and singers Tony Orlando and Dawn—and then speculate how they would react if steel needles with real sharp points were plunged into their eyes.
"[4] Later, O'Donoghue cultivated the persona of the grim "Mr. Mike", a coldly decadent figure who favored viewers with comically dark "Least-Loved Bedtime Stories" such as "The Little Engine that Died".
O'Donoghue's volatile personality and mood swings made this difficult: his first day on the show he screamed at all the cast members, forcing everyone to write on the walls with magic markers.
According to the book Live from New York, O'Donoghue tried to shake things up on that first day by saying "this is what the show lacks" and spray-painting the word "DANGER" on the wall of his office.
[7] It was planned that John Belushi would return to play Silverman, and a great deal of work had been done on creating sets for the sketch (which would have run for about twenty minutes), including the construction of a large Nazi eagle clutching an NBC corporate logo instead of a swastika.
In the sketch, a captured German officer berated by his captors for Nazi war crimes explains that he had a good excuse, which he whispers into their ears, inaudible to the viewers.
"[9] His final contribution to the show was a song, "Boulevard of Broken Balls", co-written with his wife Hardwick and performed by Christopher Walken on the October 24, 1992 episode.
O'Donoghue said he loathed the theatrical release of Scrooged, insisting until his death that he and co-writer and best friend Mitch Glazer had written a much better film.
It featured Kelly Lynch and it was directed by Walter Williams, the creator of Mr. Bill, but like a lot of O'Donoghue's work, it was too unconventional for primetime TV.
The Barnes and Noble overview read, "This is the unvarnished story of a towering figure in American popular culture, the prime artistic force behind an entire generation of humorists and satirists."