In a television series overflowing with legendary comedic performers—Amy Sedaris, Stephen Colbert, and Paul Dinello—it is a testament to the supreme comedic genius of **Greg Hollimon** that Principal Onyx Blackman routinely stole every single scene he appeared in.

As the head administrator of Flatpoint High across all three seasons of Strangers with Candy and the 2005 feature film, Hollimon crafted one of the most distinctive, quotable authority figures in American television satire.

The Chicago Second City Pedigree

Like Dinello, Colbert, and Sedaris, Greg Hollimon was a stalwart of Chicago’s legendary improvisation circuit. Performing on The Second City Mainstage in the early and mid-1990s, Hollimon became renowned for his commanding vocal presence, flawless deadpan timing, and ability to deliver absurdities with total institutional gravity.

When Paul Dinello and Mitch Rouse were casting the pilot of Strangers with Candy in 1998, they knew that Flatpoint High needed an authority figure who did not feel like a cartoon. Hollimon brought a regal, almost military dignity to Principal Blackman—making his total administrative incompetence ten times funnier.

5 Hallmarks of Principal Blackman’s Genius

  1. The Sudden PA Announcement: Blackman’s morning loudspeaker broadcasts were erratic, menacing, and filled with non-sequiturs: “Attention Flatpoint students: the following cars have had their tires slashed… because I felt like it.”
  2. Casual Bribery & Pragmatism: Never above accepting a modest gratuity or a catered meat platter in exchange for overturning academic suspensions.
  3. The Interrupted Office Conference: Jerri Blank’s disciplinary meetings in Blackman’s wood-paneled office inevitably devolved into Blackman confiding his own personal financial and romantic grievances to a confused teenage ex-con.
  4. Vocal Precision: Hollimon possessed an extraordinary baritone voice that resonated with theatrical weight, contrasting brilliantly with Stephen Colbert’s shrill, anxious falsettos.
  5. The Unflinching Stare: Hollimon’s ability to hold an awkward, silent pause on camera for five seconds without breaking character remains a masterclass in comedic confidence.

Blackman’s Greatest Hits

  • “Jerri, you’ve got a lot of nerve coming into my office without an appointment… and without a ham.”
  • “Now, I’m not saying the school is broke, but if anyone finds my toupee near the boiler room, there is a ten-dollar reward.”
  • “This school has a zero-tolerance policy for violence. Unless it’s sanctioned by the athletic booster club, in which case: break some bones.”

Hollimon’s Enduring Legacy

Following Strangers with Candy, Hollimon continued to grace film and television, appearing in The Cherokee Kid, The Ice Harvest, and numerous independent productions while remaining an indispensable mentor and performer on the Chicago improv stage.

Among comedy purists and satire historians, his performance as Onyx Blackman remains a touchstone of character comedy: an authority figure so profoundly indifferent to reality that he elevated bureaucratic neglect into high art.

Archival Cross-References