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Going for the more obscure: Bajillion Dollar Properties. Originally made for a dead streaming service, now exists on PlutoTV for free (and can be purchased through Apple et al). It's a satire of real estate reality shows with phenomenal guest stars throughout. Main cast includes a few folks before they got their bigger roles (like Tawny Newsome, Drew Tarver, and Eugene Cordero) but also includes the GOAT, Paul F. Tompkins.
Very related, I would also suggest the Comedy Bang! Bang! TV show that ran for 5 seasons on IFC. It's a treasure trove of comedic goodness, lots of great guests, and who doesn't love Reggie Watts, Kid Cudi, then Weird Al as the band leaders??
If we're talking Paul F. Tompkins we should also recommend the original run of Mr. Show (starring Bob Odenkirk and David Cross). A hilarious and extremely influential sketch comedy show.
And if we mention David Cross we should also recommend the original seasons of Arrested Development. One of the most well written sitcoms ever.
Believe me, I'm always down to talk about Paul F. Tompkins! I thoroughly agree with both recommendations, with a note that some bits don't hold up super well. But for the most part they're both still golden!