October Movies Part 1: My Old Ass, Sing Sing, Wolfs, Saturday Night

So far, October has been a bit more promising on the TV front than movies. But there are still some options for you in the theater or on streaming so let's get to them!

My Old Ass: This is a genuinely wonderful movie that people should be watching in droves. It has flown a bit under the radar because it doesn't have any big-name stars attached apart from Aubrey Plaza, but it is a sweet, funny, and moving film. Written and directed by Megan Park, it tells the story of 18-year-old Elliott (the brilliant Maisy Stella), who is spending her last summer at home with her family on their idyllic cranberry farm before she leaves for university in the big city (Toronto!) and can finally begin her life. When she does shrooms with her best friends, she has a trip where she is visited by her 39-year-old future self (played by Aubrey Plaza). Future Elliott has some good advice, mostly around cherishing this time she has left with her family, and to not be so desperate to grow up. But there is also some more cryptic advice that you will spend the rest of the film worrying about until the surprising conclusion. 

This is one of those films where you shouldn't pay too much attention to the science fiction implications of time travel: future Elliott puts her number into present Elliott's phone as "My Old Ass" and the two of them are still able to communicate after she is done tripping - don't think about that too hard. Instead, just go along for the splendid ride to experience a beautiful story about living in the present and not worrying too much about the ramification of your choices. Also, Elliott is unapologetically gay and has a great support system, so this is a great movie for queer kids and other folk who would like to just enjoy the fantasy of seeing a gay kid live their life without too much drama. This is a gem of a film and while it seems too small to get much recognition at awards season, I do dearly hope it might get a nod for Park's screenwriting or Stella's lead performance. Everyone, please run to the theater and watch it immediately.

Sing Sing: Speaking of powerful lead performances, it should come as no surprise that Colman Domingo is great in this film. Directed by Greg Kwedar, who co-wrote the screenplay with Clint Bentley, this is the story of the real-life Rehabilitation Through the Arts (RTA) program at Sing Sing prison in upstate New York. This program has been running for almost 30 years, and the focus of this film is on  John "Divine G" Whitfield (Domingo), a prisoner who joined RTA and became a playwright and director, while he also fought his wrongful conviction and tried to secure his release. Clarence "Divine Eye" Maclin also co-stars as himself, and we get to see how Divine G scouted him to join the RTA program, gradually molding him to become a star actor in the program, after overcoming his initial skepticism.

This is a film about the transformative power of the arts and the important work RTA does to get these prisoners to process their emotions and learn new ways to express themselves instead of the old standbys of anger and violence. Sing Sing is a maximum security prison, and many of these men are serving life sentences with little or no hope. But participating in RTA gives them joy and a new purpose in life. I listened to a podcast with Maclin and it's wonderful to hear this man, who had such a rough start in life and was sentenced to 17 years in Sing Sing for robbery, speak about what this program did for him and how he is now taking the work forward by helping prisoners and at-risk youth with these skills. I can't say that I always found this movie engaging, but the actors (most of whom are actual RTA alumnae) are captivating and the story they are telling is compelling and important. And the final scenes when you get to see some of the real-life plays that RTA put on through the years is enough to make you believe in humanity after all.

Wolfs: Oof. Written and direct by Jon Watts, and starring George Clooney and Brad Pitt, you would have thought this movie would be great. But it's an Apple TV+ production and is "aggressively mid" as I once heard NPR's Linda Holmes describe a lot of their catalogue. Clooney and Pitt are playing "fixers" who get called into a Manhattan District Attorney's hotel room when she accidentally finds herself with a dead body and doesn't know what to do next. She called Clooney, while Pitt was called in by the hotel owner, and now these two lone wolves must work together to clean up the situation. Which leads to a wild night across New York City as they unravel the plot of how this "dead" man ended up in that hotel room, and other tangled conspiracies that ultimately relate to who they work for in the first place. 

Honestly, I cannot tell you much more beyond that, because I barely understood this convoluted plot, the cinematography was so dark I could barely see any of the action, and apart from the very end, in a diner scene, when it felt like I could finally see Clooney's facial expressions and be reminded me of why he's such a great actor, I was thoroughly bored. I was expecting the two leads to recapture the old Ocean's Eleven magic, but their banter felt forced, and every line of dialogue just fell flat. Pitt also seems to be an increasingly sketchy public figure who needs to account for his terrible behavior towards Angelina Jolie and their children, and while he ordinarily whitewashes his reputation by producing excellent movies, this movie is such a dud that his luck has run out. So don't bother watching this film, and let's just all band together for a Pitt boycott instead. That would be a much more worthy use of our time.  

Saturday Night: Directed by Jason Reitman, who also co-wrote the screenplay with Gil Kenan, this is a movie about the 90 minutes preceding the airing of the very first episode of Saturday Night Live in 1975. As we swoop through the studio and Rockefeller Center, following creator Lorne Michaels (played by Gabriel LaBelle) around as he deals with recalcitrant actors, peeved writers, a righteous censor, eager comedians, doubtful studio executives, and...a llama, it's an absolute whirlwind of chaos. As someone who watches SNL every week and is a fan of the many iconic comedians and characters that got their start on this show, this movie is a veritable who's who of famous names. But it felt like watching The Bear, an anxiety-provoking hellscape where you just want to be like "man, is this even worth it." And oddly, it also felt like watching Studio 60 on the Sunset Strip, where everyone's laughing at the supposedly hilarious sketches, while I just sat there thinking, "huh, this doesn't seem that funny." 

Obviously, SNL is an institution, and that first episode WAS really funny and led to this show still being on the air 50 (!) years later. But this movie is such a hagiography, such a self-aggrandizing piece of "yeah, it's us against the establishment, man!" that it's a bit hard to swallow, given that SNL now IS the establishment. The movie is trying to convey how this scrappy little show was going up against the Tonight Show with Johnny Carson, with all these counter-culture comedians that no one had heard of, and it was so risqué and daring. But in the cold, hard light of 2024, it no longer feels fresh or innovative, a lot of the jokes feel sexist and tired, and apart from Lamorne Morris's delightful turn as the lone Black cast member, Garrett Morris, this just feels like a sea of white people patting themselves on the back for sticking to their guns. I really did want to like this movie, and while I do think it's a technical marvel with the way it conveys all the frantic energy and endless fires (figurative and literal!) that Lorne has to put out until this show can finally go live, it ultimately didn't seem to have anything new or exciting to say. Which is probably what most people say about SNL these days.