The Grinder: “Grinder V. Grinder”
(Episode 1.13)

Actors appearing as skewed versions of themselves in TV guest spots has been going on for years. Sometimes it works. Other times it feels fairly obvious and facile. However, in the grand history of actors playing “themselves,” perhaps nobody has been better than Timothy Olyphant on The Grinder, and this week’s episode was the pinnacle of Olyphant’s time on the show.
As you may or may not know, in the world of The Grinder, Olyphant is starring in the new show The Grinder: New Orleans, where he plays Mitch Grinder’s brother Rake. He’s also dating Claire, and so, when you put everything together, Dean and Tim have a bit of a feud going on. What makes Olyphant so great on this show, aside from his talent, is that he’s not playing things broadly. He fits into the silly, meta world of the series, but he’s also not playing an implausible version of a real actor. He’s not Neil Patrick Harris in the Harold and Kumar movies. He’s basically Dean, but he’s a guy we’ve seen in actual stuff.
When Olyphant starts hanging around the law office, and giving out advice based (much like Dean), on his TV work, everybody starts getting annoyed. Even Todd! Fortunately, Stew and Claire hatch a plan to get both Dean and Timothy Olyphant out of the office a bit, by turning them against each other. This backfires, though, when Tim starts hitting up Dean for advice on how to act like a lawyer. Of course, he teaches him all of the important stuff—how to underplay your actor. How to take your sunglasses off for maximum effect. Suddenly, the two are buddies, and they are both weighing in on things.