Over the past few years I’ve made a concerted effort to watch lots of movies considered to be among the best of all time. Now, for the first time, I’ve made my own list of favorite movies of all time. Every other Wednesday throughout 2022, I will be revealing ten movies in my list of 250 Favorite Movies of All Time.
Director: Rick Famuyiwa
Cast: Shameik Moore, Tony Revolori, Kiersey Clemons, Kimberly Elise, Chanel Iman, Tyga
Blake Anderson, Zoë Kravitz, ASAP Rocky
When did I first watch this movie?: July 2016
Why is this one of my all time favorites?: The teen coming-of-age comedy is updated for the 2010s when a pair of nerdy Black teens get caught in the middle of a drug deal gone wrong and have to use their wits to outfox gang members and the authorities. It’s a fun but thoughtful take on some old tropes.
Title: Pee-wee’s Big Adventure
Director: Tim Burton
Cast: Paul Reubens, E.G. Daily, Mark Holton, Diane Salinger, Judd Omen
When did I first watch this movie?: In the theatres, summer of 1985
Why is this one of my all time favorites?: I’ve read that Pee-wee’s Big Adventure has the “perfect script.” It’s 90-minutes long, a crisis occurs 30 minutes in (Pee-wee’s bike is stolen), and the crisis is resolved 60 minutes in (Pee-wee finds his bike, then he has to recover it). Whether or not that is true, this movie is an absurdist masterpiece, and an endearing comedy which ties together a series of gags that all still hit almost 40 years later.
Title: Arsenic and Old Lace
Director: Frank Capra
Cast: Cary Grant, Raymond Massey, Peter Lorre, Priscilla Lane, Jack Carson, Josephine Hull,
When did I first watch this movie?: Some time in the mid-1980s
Why is this one of my all time favorites?: Speaking of absurdist masterpieces, this movie features a great performance by Cary Grant as the straight man in a family of literally insane people who has to deal with the discovery that his gentle, elderly aunts are serial killers.
Title: Star Wars: Return of the Jedi
Director: Richard Marquand
Cast: Mark Hamill, Harrison Ford, Carrie Fisher, Billy Dee Williams, Anthony Daniels, David Prowse, Kenny Baker, Peter Mayhew, Frank Oz
When did I first watch this movie?: In the theaters in May 1983
Why is this one of my all time favorites?: This was the much-awaited finale of the original trilogy of Star Wars movies, and one that paid off a lot of the threads that had been developing with exciting action and drama. A lot of people hate the Ewoks, but I think it was a brilliant twist to have creatures so innocuous-looking that the Emperor would never foresee their alliance with the Rebels would be a turning point.
Title: 10 Things I Hate About You
Director: Gil Junger
Cast: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Larry Miller, Andrew Keegan, David Krumholtz, Susan May Pratt
When did I first watch this movie?: January 2020
Why is this one of my all time favorites?: Another classic teen movie, this time updating Shakespeare’s Taming of the Shrew for the 1990s. Stiles and Ledger have the chemistry that sells the humor and the romance of this movie.
Title: The Philadelphia Story
Director: George Cukor
Cast: Cary Grant, Katharine Hepburn, James Stewart, Ruth Hussey, John Howard, Roland Young, John Halliday, Mary Nash, Virginia Weidler
When did I first watch this movie?: In my college days in the early 1990s
Why is this one of my all time favorites?: Perhaps the perfect screwball comedy featuring romance and hijinks among the Philadelphia Main Line set. The trio of Grant, Hepburn, and Stewart is possibly the greatest collection of stars at the top of their game ever to appear on film.
Title: Winged Migration
Director: Jacques Perrin, Jacques Cluzaud, Michel Debats
Cast: So many birds
When did I first watch this movie?: Circa 2003, on DVD
Why is this one of my all time favorites?: This thrilling nature documentary follows the migration of various flocks of birds using new technology to “fly” alongside them. I’ve always meant to rewatch this on a big screen as it deserves to be seen
Title: Groundhog Day
Director: Harold Ramis
Cast: Bill Murray, Andie MacDowell, Chris Elliott
When did I first watch this movie?: In college, early-to-mid 90s
Why is this one of my all time favorites?: This movie basically invented a new sub-genre of time loop romantic comedies, but it still remains the best. Bill Murray is at his comic peak and also begin to expand his acting range. And there are so many memorable gags and quotable lines.
Title: Hope and Glory
Director: John Boorman
Cast:Sarah Miles, David Hayman, Derrick O’Connor, Susan Wooldridge, Sammi Davis, Ian Bannen, Sebastian Rice-Edwards
When did I first watch this movie?: Late 80s
Why is this one of my all time favorites?: The movie is a delightfully nostalgic piece about growing up in a horrible time: London, during the Blitz. It’s a great comedy about the community that grows up on the home front during times of strife.
Title: The Great Dictator
Director: Charles Chaplin
Cast: Charlie Chaplin, Paulette Goddard, Jack Oakie, Henry Daniell, Reginald Gardiner, Billy Gilbert, Maurice Moscovich
When did I first watch this movie?: September 2019 for my original Classic Movies project
Why is this one of my all time favorites?: Speaking of World War II, Charlie Chaplin’s first full-talkie movie is this outstanding send-up of fascism and dictatorship that remains frighteningly relevant in our time.