Updating my rankings, since I've re-watched all the TNG Movies last week. They help put the Picard seasons into better context, at least for me. Rounding off to the nearest point on a 10-scale.
1. "The Best of Both Worlds" --> 10
The best TNG Movie technically wasn't a movie. I saw it in a theater in 2013, so it counts as far as I'm concerned. A major turning point in Picard's life, a major turning point for the Federation, looks at Riker's career, and it has Shelby challenging Riker from within while the Borg challenge the entire crew from without. Works on so many levels. The Ron Jones score sells it perfectly.
2. Star Trek: First Contact --> 10
TNG on the Big Screen, with a ship and sets built for the Big Screen. Follows up on Picard's trauma from BOBW, shows First Contact between Earth and Vulcan, introduces the Borg Queen, has some really raw scenes, and cuts right down to whether or not Humanity in the 24th Century actually really is as evolved as Picard says, and puts a microscope right up to that claim.
3. Picard Season 3 --> 9
Follows up on the entire TNG crew 20 years after Nemesis and sees how their lives have moved forward. Vadic has a charismatic Prescence. Shaw is a great addition who challenges Picard and Riker in a critical way, but also has flaws including the way he treats Seven. The season shows how Seven adjusts to actually being an actual Starfleet Officer as opposed to her time with the Fenris Rangers or a newly liberated ex-drone on Voyager. It also shows how Picard comes to terms with having a son and takes the Picard/Crusher relationship further than I ever expected to see. We get to see what Riker is actually like as a seasoned Captain for more than just the one scene we had in Season 1. I liked the reveal that Borg had a multi-layered plan where Picard could still lead to the assimilation of Humanity through offspring even after he was rescued from the Collective in BOBW. I liked how Shaw served as a reminder that more people suffered at the hands of Locutus than just Sisko. Loved how Picard's statement about Starfleet being "the only family I ever needed!" could be read on two levels: one it sounds great because he doesn't know about Jack, but to Jack that sounds really messed up, and then Picard thinking back to that moment and realizing the weight of what he actually said. And so many other things I've already pointed out before. I didn't even mention the D. This is getting too long....
4. Picard Season 1 --> 9
I liked that this season wasn't afraid to take Picard out of the context of Starfleet, the Enterprise, or his former crew, and dropped him into La Sirena on a mission unsanctioned by Starfleet to find Data's "daughter" and Dahj's "sister" Soji. This season masterfully wove the pieces left behind by Nemesis, the future scenes in "All Good Things", Spock Prime's recap of 2387 in Star Trek (2009) to create the world of 2399. La Sirena's crew was as different from the Enterprise-D crew as you could get. I also loved getting a different take on Seven of Nine, who's been hardened by her experiences since Voyager returned to the Alpha Quadrant. Best of all, this season had the best developed Romulans I've ever seen. It took everything we ever knew, saw, or heard about the Romulans and took it to another level.
5. Picard Season 2 --> 8
I enjoyed all the episodes on an individual level, even though the whole didn't quite add up, but I loved seeing the Confederation. I loved seeing a Borg Queen who wasn't obsessed with revenge, we got to see a version of her in a completely different context. I liked the 2024 scenes and some of the stuff other people didn't like I enjoyed, including the Car Chase. That actually had me on the edge of my seat. I loved when Picard and company crashed the NASA gathering on the night before Renee Picard's mission. It felt like an episode of Mission: Impossible (that series, BTW, is much better than the movies and was Star Trek's sister show in the '60s, so I recommend watching it if you have seen it). Seven and Raffi make a great duo. Rios's easy-going budding relationship with Teresa was nice to watch. Brent Spiner was perfect antagonist as Adam Soong. The storyline with Q could've used some work, but I did enjoy his scenes with the aforementioned Adam Soong. Penelope Mitchel was effective as Renee Picard. Orla Brady was great as Tallinn. If the writers couldn't find much for her to do as Laris, I'm glad they found more for her to do as Tallinn. Ito Aghayere was okay as a Young Guinan if you look at her as her own character, but she didn't really come across to me that well as a younger version of Whoopi Goldberg. I appreciated that this season wasn't afraid to look at Picard's past, and was able to directly contrast his mother as seen in "Where No One Has Gone Before" with his father as seen in "Tapestry", because they really did seem so different from each other. Kore was pretty much a different spin on Dahj and Soji where she thought she was one thing and found out she was really something else. All I have to say about the season. A lot more positive than people give it credit for. And a shout out to Lea Thompson for directing and making an appearance!
6. Star Trek: Generations --> 7
It's not a bad movie, it's just an uneven movie, and I don't think this was the best story to introduce TNG to for a movie audience if they hadn't watched the TV series. The cinematography is great, the lighting is moody, it was great to have Kirk meet Picard, but a lot of what's in the movie seemed too much like a checklist of things, which it was, but at least it had ambition and aimed for a story with a larger scope, unlike...
7. Star Trek: Insurrection --> 6
Sounds cliche to say this, but it's true: this feels like a middling episode with a movie-sized budget. That was always true, but now, in the time since January 6th, 2021, when we've seen an actual insurrection attempt, it makes this movie look tame compared to what it could've been. As it is, the film is pretty to look at, has nice effects, and is inoffensive... except during the flesh-stretching scenes!
8. Star Trek: Nemesis --> 5
I was going back-and-forth on whether or not to rank Insurrection last or Nemesis last, but I went with Nemesis. Insurrection didn't aim high whereas Nemesis aimed high and failed. I can't rank based on effort (in which case NEM wins), I have to rank based on what I see. And what I saw left me feeling in a dour mood when I walked out of the theater in 2002. The TNG Movies could've recovered from Insurrection. Nemesis killed TNG for almost two decades. It also killed my own interest in any further TNG until Picard came along, and I can't just ignore that. But the movie wasn't a total loss. It had its moments, and the soundtrack was some of Jerry Goldsmith's best work, but it just wasn't enough. Unlike in Picard Season 1, the Romulans here felt lackluster. The Remens did nothing for me. And Shinzon was boring. B-4 was annoying. The character moments among the TNG crew rise the movie. If someone did a fan-edit that focused on all the character moments, restored all the deleted scenes, and cut all the mind-numbing action scenes by half to two-thirds, it would've made for a much better movie.