Captain America: The First Avenger (2011)
As a classic movie fan I'm a sucker for the 1940s setting of this first Captain America adventure, but it's the heart of this picture that brings me back again and again. Chris Evans is perfectly cast as an old-fashioned good guy with a steady moral compass, and I simply adore Hayley Atwell as Peggy Carter (I'm still bitter about the cancellation of Agent Carter). Sebastian Stan begins a long but engrossing character arc as Steve's friend, Bucky, and it's refreshing to go back to this first outing and see him before his dark period in the Winter Soldier role.
Even though Edgar Wright left the project and was replaced by Peyton Reed as the director, Wright's distinctive sense of humor is still readily apparent in this smaller scale Marvel hero origin story. The zippy comedy, heist movie tropes, and casting all make this one a hit for me, and I also love its soft center theme of fathers who love their daughters. Paul Rudd, recently crowned the 2021 Sexiest Man Alive by People Magazine, deserves a lot of credit for merging the comedic and dramatic demands of his role as Scott Lang. The supporting cast of loser ex-con buddies is so much fun that it's great to see them reunited in Ant-Man and the Wasp (2018), and I hope we'll see them again in the upcoming Quantumania sequel.
Doctor Strange (2016)
Here's another pick that has a lot to do with my personal preferences as a fan; I love the supernatural side of both DC and Marvel comics, and I really enjoy Benedict Cumberbatch's work in general, so Cumberbatch joining the MCU as the Sorcerer Supreme is a real treat. The What If...? Disney Plus series has shown us that Stephen Strange's journey could have taken a much darker route, but in the main timeline story we see him develop as a character and overcome his hubris, despair, and frustration. Benedict Wong is a scene stealer as Wong, and I really enjoyed seeing him return for Shang-Chi. I also appreciate the fact that Dr. Strange saves the day not by fighting and punching but basically by annoying his opponent until Dormammu finally gives up. In a universe full of muscle gods, a hero who thinks his way through a problem deserves special attention.
Thor: Ragnarok (2017)
Speaking of muscle gods, here's Chris Hemsworth back in the fray as Thor in the third and by far the best of the Thor stories to date. A hilarious script and direction by the brilliant Taika Waititi make all the difference in this picture, although it also has a fantastic cast, great action scenes, moments of grand dramatic gravitas, and some truly inspired use of Led Zeppelin. Jeff Goldblum runs away with his scenes, giving regular scene stealer Tom Hiddleston a run for his money, and Tessa Thompson is brilliant as Valkyrie. Cate Blanchett radiates gleeful malevolence as Hela, an Asgardian so dangerous and twisted she makes Loki look like a saint. If I were ranking these five films by preference rather than release date, Thor: Ragnarok would be my top pick. It's just that much fun.
Black Panther (2018)
It's not just respect for the tragically short career of Chadwick Boseman that makes me include this movie in my five favorites; it's a gorgeous, riveting action picture with a fabulous cast and a fascinating glimpse of Afrofuturism that sets it apart from all of the earlier Marvel movies. Boseman is pitch perfect as T'Challa, but the movie provides such good roles for women, too, especially Danai Gurira as Okoye and Letitia Wright as Shuri. The MCU has come a long way from Black Widow as the only girl in the boys' club, but Black Panther does a particularly good job of showcasing different female characters, with different talents, attitudes, and relationships, and even though I will miss T'Challa I'm excited to see where Wakanda Forever will take the remaining characters.
I thoroughly enjoyed Shang-Chi and the Legend of the Ten Rings, and it might well displace one of these older movies in my top five over the next few months, but it's too early to say how many times I'll feel drawn to rewatch it. 2022 will bring us a lot of sequels featuring heroes we've already met, so we'll see if those stories can beat the appeal of the previous installments!