This is Dean Pelton, a character played by Jim Rash on NBC's "Community."
This is Richard DeLongpre, a character voiced by French Stewart on FOX's "Allen Gregory."
I am not the first person to note a similarity -- before I watched the first episode of "Allen Gregory" a friend of mine told me, "Allen Gregory's parents are 2 men! One of them is the dean from Community." Even after I realized his error while watching the episode, the other friend watching it with me said "Is that the dean from Community?" If you google, say, the terms "Dean Pelton" and "Allen Gregory" together, you'll see that this has been pretty widely noted discussed (although some, apparently, have compared DeLongpre to another bald, bespectacled cartoon character, Rusty Venture from "The Venture Bros.")
Here is small contribution to this conversation that I haven't seen anyone else make note of yet:
This is Jeremy, Richard DeLongpre's life partner on "Allen Gregory," voiced by Nat Faxon. The show frequently implies that the handsome Jeremy was a straight man that Richard initially forced into a gay relationship, which aside from being one of the many really strange and discomforting plot elements on "Allen Gregory," brings up another "Community" parallel, since the sexually ambiguous Dean Pelton has often seemed attracted to the show's handsome main character, Jeff Winger, and over time the show has been more overt about Dean Pelton being clearly gay and sometimes deliberately forcing Jeff Winger to spend time with him in somewhat romantic or sexual situations.
Now here's the weird part:
Here is Jim Rash, the Dean Pelton actor and Richard DeLongpre doppelganger, with Nat Faxon, the actor who voices Jeremy, Richard DeLongpre's life partner. In real life, Rash and Faxon are longtime collaborators and writing partners, who wrote the screenplay to the new George Clooney movie The Descendants together. You have to wonder if Faxon was ever aware of the similarities between these characters as he worked on "Allen Gregory," or if perhaps there was ever plans for Rash to voice DeLongpre, something that NBC could've nixed since "Community" upgraded Rash to a regular cast member this fall, around the same time "Allen Gregory" debuted on FOX.