Midway through its first season, The Grinder has been blessed with an unusually large number of high-profile guest stars. Hardly an episode goes by without a West Wing mini-reunion or a Timothy Olyphant visit to Boise. Sometimes this is a strength, other times it's a weakness, but I'm interested in a deeper question. Do the showrunners consider guest roles to be part of their formula, or just a thing they enjoy doing?
If I had to hazard a guess, I'd say it's the latter. "The Retooling of Dean Sanderson" has three notable guest stars, and only one — Colton Haynes, playing the on-screen son of Mitch Grinder who suddenly appears in The Grinder's fourth season — seems like the actual actor's career was part of the joke. (Shoutout to Teen Wolf and Arrow fans, as well as fans of sullen young men with excellent bone structure.)
The other two prominent guest stars are Jim Rash and Maya Rudolph. Rash plays Bill Foosly, a big-time auto dealer in the market for new legal counsel. Rudolph plays Stewart's therapist, Jillian, who inadvertently complicates Stewart's life when he recommends that Dean start seeing her.
Sanderson and Yao wants to attract new clients, so Papa Sanderson asks Stewart to take Foosly to dinner and win his business. Dean, however, believes that his brother does not have the level of pizzazz necessary to wow Foosly, and insists on coming along. This prompts Stewart to approach Dean in his new office — he's set up shop in Yao's old office, just because — to talk to him about how he needs to stop being the character he played all the time. He points out Dean's tendency to bring stuff from the TV show into the real world. Dean takes hardline stances like, "The Grinder never settles," when in reality, real lawyers settle a lot.
Stewart: Some of that stuff is not okay here.
Dean: But what if it was?
Stewart: See, I don't even think that you know when you're doing it, and that is really what concerns me the most.
Dean is taken aback by this criticism — to him, it's coming out of nowhere. Stewart suggests he try therapy, if only to dial down his Grinder-ness in their day-to-day lives. Dean agrees to the latter, but not the former.
Unfortunately, it doesn't seem to help much at all, because in the middle of Stewart's seemingly successful dinner with Bill Foosly, Dean chooses to interrupt with one of his trademark dramatic entrances. He then tries to win Foosly over with his charisma, but it doesn't work. And, naturally, Dean doesn't listen to anyone who tells him it's not working.
Dean: Hush. The foreplay is not over yet.
Bill: Eww … wait, were you at the bar this whole time just waiting to interject at the perfect moment?
(Sadly, Jim Rash's delivery of "eww" is one of the few moments where Jim Rash gets to display his Jim Rash-ness.)
Foosly is creeped out by Dean — a Boise first — and after complimenting Stewart's evident legal skill, says he's going to take his business elsewhere. Dean is too huge of a liability.
Even Dean can see he's screwed things up, and therefore agrees to begin therapy with Jillian. Like every other plan Stewart has had, this does not work out the way he hoped. Dean, for his part, is very gung-ho about it: "I am in therapy to win therapy," he declares to Jillian, "I need to make sure you're on board with that."
Dean finds therapy to be completely transformative, and later that night, he announces to the family that he's going approach things differently now. To prove it, he addresses Deb, telling her that he's never really been involved in her life because nothing grabbed him. There was no drama. He wants to change all that now — not because she's any more interesting, but because she's boring. Then, he starts talking about her work problems. We know she's caught between two bosses who don't communicate with each other, but Dean doesn't know that. She doesn't get a chance to explain, either, before Dean starts parroting what Jillian told him about taking the wheel of his own life and being responsible for his own happiness.
This scene could be read as a self-deprecating bit of meta-commentary — the show has never really known how best to make use of Deb, and seems to want to do more with her. We even get a glimpse of her work life in this episode! But, just like Dean cuts Deb off to parrot Jillian's advice, The Grinder isn't really committed to exploring Deb's character. She remains adjacent to most of the comedy, not the source of it.
At the firm the next day, we find out that Foosly wants to give them another chance — and Dean wants in it. He wants to apologize. There's a lot of protesting, but Dean pretty much always gets his way, so he's at the next dinner. Claire comes too.
Except this time, Stewart is the liability. He has to excuse himself when Deb calls him; she followed Dean's advice and just quit her job. Stewart is plenty upset that she didn't talk to him before quitting, and that she took advice from Dean.
Dean, however, is on a roll. He's talking to Foosly about his problems, and Foosly is totally into it. When Stewart comes back visibly agitated, they all assume the worst and want to talk about his problems, too! But Stewart's default state is Not Chill, so he gets even more agitated and ends up grabbing Foosly's wrist when he asks for the check, thereby losing the client a second time.
But that's the least of Stewart's problems. At the office the next day, Papa Sanderson announces that someone is suing for malpractice … and coming after the whole damn firm.