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LOVED this show, although somewhere in the deep middle it felt a little sloggy to me. But it perked up here in the last season, and I give the series two thumbs up.
You're right about Rachel finding the right role. I too was a bit stunned when I looked her up on IMDb that first season (because she looked familiar), only to realize she'd played Rachel Posner on House of Cards. Polar opposites. If someone had told me while I was watching House of Cards that she'd eventually be starring as a 1960s comedienne, I wouldn't have believed it. But her comic timing when her character was onstage was always razor sharp.
I absolutely loved all the side characters too: her parents (gotta love Tony Shalhoub!); her in-laws; Susie; the maid... everybody was fabulous in this show. Adding in Lenny Bruce was an interesting way to go mid-series, and it made for some great moments. The sets were terrific; the costumes were glorious. Everything = so fun, so well done.
I did NOT mind that final scene in 2005 because I'm betting it was a sort of sideways homage to the likes of Mel Brooks and Carl Reiner, who often met for dinner and to watch shows like Jeopardy and Wheel of Fortune around takeout food and cheap dinners. When Reiner died, I immediately thought that Brooks was probably going to feel a very deep hole in his life without having Reiner around to get together and watch game shows each evening.
I don't think they overdid it--just one scene, after all. The diner scene I could have done without, but it kinda brought the Lenny Bruce elements full circle, so that too didn't seem overdone.
As for the flash-forwards this season: I could take them or leave them. They did kinda give away the fact that she did end up successful, and some of the scenes with her grown son/daughter were awkard because those relationships were a bit sad. And of course, Joel ending up in prison to protect her was just such a heart-wrenching thing. And yet, why didn't we see him in/around 2005? Did they ever show us what became of him? Did that slip past and I missed it? There were SO many times I was sure we'd see them get back together, but yet it never happened. Despite his having gone to prison for her!
ANYWAY, sad to see this show end, but it did, at least, end properly. Too many shows get cancelled without closure, so I'm grateful when a show can tell its own story and finish it on its own terms.