December 27, 2024
As I was thinking through my last post of the year and ideas for next year, I had this “Holy shit” moment when I realized that I started this little hobby five years ago. On the one hand, if you look at the number of films I’ve watched over that timeframe (too many to admit to in a public forum), it’s not that surprising. But still, I’m quite proud that I’ve kept this endeavor moving forward, especially during those times when I couldn’t seem to get out of my head in trying to craft a sentence. Closing the laptop and doing something else was clearly the right move in those instances.
With the year winding down, I’m already starting to plan out 2025’s topics, which will include a look at one of our greatest living actors, a hair-brained idea that I am not sure I can pull off, as well as a topic I just didn’t have time to get to this Christmas (Sorry, Annie.) And I will continue to cover new releases each month. My 2025 movie list is insanely long right now. Let me tell you – next year’s slate looks fantastic. I know many people are still catching up on 2024’s wonderful movies, especially ahead of the coming awards season. I will be covering my look at my favorite films of 2024 starting in January, so stay tuned for that. But first, here is part two of my look at the best movies of 1999, at least in this fan’s opinion. If you missed part one, you can find it here.
Those Crazy Teenagers
One of the fun things about looking back at a movie year is to see how certain actors or filmmakers have developed since then. At the top of the list for this endeavor is Reese Witherspoon, who had two films released in 1999 and would go on to build an excellent career as an actress (including an Oscar win for her wonderful performance as June Carter Cash in 2005’s Walk the Line) and producer. Witherspoon was still relatively early in her career in the late 1990s, having impressed audiences since her debut in 1991’s Man in the Moon. Her two films in 1999 could not be more different from each other.
First up is Cruel Intentions, a movie that I would affectionately refer to as a trashy remake of Dangerous Liaisons, set at a New York City prep school. Witherspoon plays the new girl at the school, who is pursued by bad boy Sebastian, played by Ryan Phillippe (onetime husband of Witherspoon – they met while making this movie.) He is coerced into the chase by his stepsister Kathryn (played by Sarah Michelle Gellar), who Sebastian also wants to get into bed. Did I mention this movie was trashy? It’s quite ridiculous and definitely a product of the 1999 culture. I wouldn’t go out of my way to call Cruel Intentions “good” or recommend it, but it has a fantastic soundtrack, which I covered in my piece about my favorite movie soundtracks, and a key reason I still have affection for it.
Next up is one of my favorite movies of all-time, the black comedy Election, with Witherspoon as Tracy Flick, who will stop at nothing to win her class president election. This is the film that showed Hollywood that Witherspoon has fantastic range, playing the determined, whiny, and cutthroat Flick with fierceness and humor. Standing in Tracy’s way is history teacher Jim McAllister (played by Matthew Broderick), who is sick of Tracy getting everything she wants and sets out to teach her a lesson in humility. Unfortunately, Jim is a bit of a dumbass with his own personal problems. Broderick is great in the role, showcasing his ability to successfully move past playing the wiseass teenager we saw so frequently in the 1980s.
Election was directed by Alexander Payne, who also co-wrote the script (based on Tom Perrotta’s novel) that received an Academy Award nomination. Payne is a terrific filmmaker, who excels at crafting a balanced combination of humor and drama, while casting the perfect actors to bring his stories to life. It’s no surprise that his films The Holdovers, Sideways, and The Descendants are beloved by critics and audiences alike. Shortly after Election, Witherspoon would catapult into superstardom with Legally Blonde, but for me, Tracy Flick is one of my favorite roles she has played. Speaking of which, there is a sequel in the works, based on Perrotta’s 2022’s novel Tracy Flick Can’t Win, with Witherspoon and Broderick likely returning. Count me in.
In 1999, two up-and-coming actresses were cast as ditzy teenage friends who are thrust into the Watergate scandal in the absurdist comedy Dick. At this time, Michelle Williams was just beginning her acting career, while Kirsten Dunst was starting to make a name for herself after starring opposite some pretty big movie stars in Interview with the Vampire and Wag the Dog. 1999 also saw Dunst play the lead role in Sofia Coppola’s excellent debut picture, The Virgin Suicides. Looking back at their performances in Dick, the actresses’ talents are on display for one simple reason – silly comedies can be terrible if the performers are not committed to the bit, but they pull it off very well.
Williams and Dunst play Arlene and Betsy, who stumble upon the Watergate break-in, not realizing the severity of what they witnessed. Nixon’s henchmen, seeing the girls as a legitimate threat, decide to offer them a job walking Tricky Dick’s dog, Checkers, as a way to keep an eye on them. The more they hang around the White House, the more they start to learn about Nixon’s nefarious deeds, and even insert themselves into U.S. history.
Now, if you are a Watergate nut like me (All the President’s Men is one of my favorite movies of all-time – I can practically recite the script every time I watch it), then you may enjoy Dick, with a big caveat. It’s very silly – like, don’t take it seriously. There are times where you will think, “wow, this is dumb,” but that’s the point. I recently rewatched the film and decided to laugh along with the goofiness of the performances of Williams and Dunst, two future Oscar nominees (and hopefully winners someday.) There are also a number of recognizable faces playing Nixon’s White House staff and other supporting characters. Oh, and there are some great 1970s tunes on the soundtrack that add to the Watergate-era vibe. Speaking of which…
The end of the film features a great scene as Nixon leaves office, with Carly Simon’s masterpiece You’re So Vain playing. Recently, I was listening to some music while working on my blog when I heard this tune, which is part of Questlove’s Yacht Rock playlist on Spotify. Huh? Well, he was featured in the outstanding Yacht Rock documentary that recently premiered on HBO and Max. It’s a fascinating look at the 1970s and 1980s music scene featuring artists like Michael McDonald, Toto, Steely Dan, Kenny Loggins, and others that would be collectively referred to as Yacht Rock several decades later. The film includes interviews with many of the musicians as well as other contemporary artists, like Questlove. He mentioned that he created a Yacht Rock Playlist that has become very popular.
I’ve been listening to these tunes the last few weeks and while I’m loving this music, I have to be honest –occasionally I flash back to hearing WRCH 100.5 (how the hell do I remember that? My brain is broken) the light music station my father listened to when I was a teenager. Holy shit, am I officially old now? I’ll be right back – I need to go buy some concert tickets…. Speaking of which, I have officially launched a plot to return to the Gorge next year. Let’s see if we can make it happen. Anyway, if you want a silly teenage comedy, check out Dick, and I highly recommend Yacht Rock: A DOCKumentary if you are a fan of music documentaries and tunes from that era.
The Tapestry of Life – Magnolia
How lucky are we to have a new Paul Thomas Anderson film coming to theaters in 2025? Not much is known about the picture, except it stars Leonardo DiCaprio and will get an “event-sized” release from Warner Bros. Studios, including IMAX theaters. Let’s f-ing go! Could this be the film that finally lands Anderson an Oscar? OK, I’ll calm down until we see it next August. In the meantime, 1999 saw Anderson release his third movie, Magnolia, two years after the outstanding Boogie Nights.
Look, I am a sucker for PTA’s movies, and covered his filmography here following the release of Licorice Pizza three years ago. Magnolia is a sprawling story of several residents of Los Angeles, who are loosely connected to each other. We have stories of love and loss, conflict, anger, depression, and even bizarre tangents that feel out of place. Anderson’s story is ambitious in scope and was criticized at the time (and even twenty-five years later) for being pretentious and bloated. The three hour runtime does feel long at times, but if you are engaged with the characters and themes, it’s worth the trip.
With so many characters, it’s natural that we will see a number of recognizable faces like John C. Reilly, Julianne Moore, Philip Seymour Hoffman (a frequent Anderson collaborator), and William H. Macy. The clear standout of the movie is Tom Cruise, playing misogynist motivational speaker Frank Mackey in a performance that should have won him the Oscar given to Michael Caine that year. Cruise was at the height of his popularity at the time and this was a risky role, playing such a despicable asshole.
Along with a film I’ll get to shortly, these are the types of roles I want Cruise to pursue going forward. Sure, I’ve loved all of the Mission: Impossible movies and Top Gun: Maverick was my favorite picture of 2022, but as he is now in his 60s, I’d love to see him pursue more character based stories that show his acting chops, much like Paul Newman did as he got older. Cruise has shown this potential throughout his career, which I covered here. After next year’s Mission: Impossible – Final Reckoning, he is starring in a dark comedy directed by Oscar-winning director Alejandro González Iñárritu (Birdman, The Revenant.) I’m hopeful that this sends him on a journey that gets him back to being more of an “actor” and less of an action star. In the meantime, Magnolia captures his talents perfectly.
The Art of Filmmaking – The Talented Mr. Ripley
Two years after winning an Oscar for co-writing Good Will Hunting, Matt Damon delivered what might be the best performance of his career. Sure, I’m a fan of the Jason Bourne series and he’s outstanding in The Departed and The Martian, but The Talented Mr. Ripley is where Damon showed his chameleon-like ability to slip into any character.
Damon portrays Tom Ripley, a con artist in 1950s New York who is convinced by a wealthy businessman to fly to Italy in an effort to bring home the man’s son. Ripley had told the man they were classmates at Princeton (the first of many lies Ripley would tell) and when he arrives, he quickly ingratiates himself with Dickie (Jude Law) and his fiancée Marge (Gwyneth Paltrow.) What transpires is a devious scheme where Ripley does everything he can to be with (or become?) Dickie and to leave his boring life behind. He has trouble keeping his stories straight, especially when Dickie’s friend Freddie (another magnificent performance from Phillip Seymour Hoffman) starts getting suspicious. Innocent lies start to pile on top of each other and before you know it, the worst kinds of crimes are committed.
Not only is the story of this film incredible, keeping you guessing how far Ripley will go to maintain his web of lies, it was beautifully directed by Anthony Minghella, in his first picture after winning Best Director for The English Patient three years earlier. The Talented Mr. Ripley was shot on location, which brings to life the Italian setting and is a reminder that when film crews go on location (instead of creating it on a computer or in front of a green screen) it makes all the difference in the world.
Damon was a revelation in this film, playing Ripley with such range – vulnerability, awkwardness, shrewdness, manipulative behavior, and downright terrifying. It is truly a “Holy shit, this guy is an incredible actor” performance, especially when you realize that this was still early in Damon’s career, and you compare it to recent roles like Oppenheimer and Air. I have always been a big fan of his work because he takes chances, works with a wide variety of filmmakers and always brings his A-game.
What’s next for Damon? Starring in Christopher Nolan’s upcoming film, which is a retelling of Homer’s The Odyssey. Hmm, interesting choice by Nolan, but I’ll trust anything that one of my favorite directors chooses to make. Co-starring in that film is a murderer’s row of star power – Tom Holland, Anne Hathaway, Zendaya, Cate Blanchett and many more. Damon was excellent in a supporting role in Nolan’s Oppenheimer. Can he be directed to a Best Actor Oscar like his co-star Cillian Murphy was? We’ll find out in 2026 when The Odyssey is released.
One more note on Ripley. The film was based on the 1955 novel by Patricia Highsmith, which was also adapted into an outstanding limited series that premiered on Netflix earlier this year. The lead character was portrayed by Andrew Scott, one of the better actors working today who should be a household name. He was outstanding in last year’s All of Us Strangers, which almost nabbed him an Oscar nomination and was just as good as Damon as Ripley. The showrunner for the Ripley series was Steven Zaillian, who has written the screenplays for Schindler’s List (for which he won an Oscar), Moneyball, and The Irishman among others. Yeah, Zaillian’s got the goods and chose to film the series in black and white. As good as the 1999 movie looks, the Ripley series is even more impressive, even on a television screen. Although you may be familiar with the story from the 1999 film, the Ripley series is one I highly recommend. Or watch them both!
Head Games
Are you looking for two mindfuck movies to program for a Friday night double feature? Have I got the choices for you.
First up is Being John Malkovich, the first movie written by Charlie Kaufman, who has had some incredible success in his career, coupled with some very strange films that didn’t work for me, as I covered here in 2020. His 1999 screenwriting debut (directed by Spike Jonze) is the story of aspiring puppeteer Craig Schwartz (John Cusack), who begins working at a company on the 7 ½ floor (don’t ask) of an office building. One day he discovers a small doorway that leads to a portal into the mind of actor John Malkovich, who plays himself in the movie, in what may be the best meta performance of all-time. Craig pairs up with his coworker Maxine, who he is in love with, to start charging people to take the “Malkovich ride,” but things get complicated quickly.
Being John Malkovich is on one hand an absurdist comedy that will twist your brain at times as you try to understand what is happening. But at its heart, the film is a story about one’s identity and the sense of self we all feel trying to determine who the hell we are. Craig just wants Maxine, and will do anything he can to get her, even if it means hijacking Malkovich’s body forever, and sacrificing his own persona in the process. Maxine has fallen for Craig’s wife Lotte, but only when Lotte inhabits Malkovich’s body. And Lotte doesn’t know what she wants.
The cast here is wonderful, particularly Cusack, Catherine Keener (as Maxine) and Cameron Diaz (as Lotte.) And you have to give credit to Malkovich for going along with such a crazy premise in agreeing to make this movie. The scene where he goes into the portal is truly mind-blowing and beyond creepy. My favorite line is when he tells Craig to shut it down, saying “It’s my heaaaaad Schwartz!” Kaufman has never been afraid to take big swings in his movies (which I like), but his best ones were directed by others like this film, along with Eternal Sunshine of the Spotless Mind and Adaptation, two more mindfuck movies you could add to your list if you are so inclined. I hope his next project is one where he partners with a director who can take his ideas and make them work on the big screen.
If your brain wasn’t already turned into a pretzel after watching Being John Malkovich, let me present to you Fight Club, the David Fincher masterpiece that blew the minds of moviegoers when they first saw it in 1999. Edward Norton plays our central figure (his character literally has no name) lamenting about his empty life as an insurance claim adjuster. He finds new meaning in the world when he meets Tyler Durden, played by Brad Pitt. When our main character’s apartment blows up, Tyler invites him to move into his dilapidated house and the two begin a new friendship. They make soap, drink beers, and start a fight club.
The first half of Fincher’s adaptation of the cult novel written by Chuck Palahniuk is focused on a character finding rock bottom before being pulled out of misery by his new circle of meatheads beating the shit out of each other. And you may be wondering where this story is going. Soon we learn that Tyler is recruiting an army of soldiers to train for his Project Mayhem, a plot to tear down the capitalist society that we have all become to depend on. Things turn progressively violent until our main character intervenes to try to stop Tyler. And then we go off the deep end, when we learn the true identity of Norton’s character and that what we have witnessed throughout the film has been a lie.
I have never read the Fight Club novel, so I can’t say how accurate the film adaptation was to the source material. But what I do know is that novels with very tricky plots that unfold at the end, especially with an unreliable narrator, are almost impossible to adapt successfully. It’s so hard to not spoil a book like that when you have to depict it on the screen. Another example of this type of challenge is the masterful adaptation of Gone Girl, which was directed by (you guessed it) David Fincher. He’s one of my favorite directors working today and Fight Club is right up there as one of his top films, as I covered here in 2020. It’s a success not only because of the clever storytelling aspect, but in the visceral way the film is shot, bringing the production design to life so we can feel the sweaty, grimy life that these two lead characters are leading. My favorite anecdote about Fight Club was told by Pitt in an interview. He said that when the movie premiered at the Cannes Film Festival in 1999, the crowd booed. He leaned over to Norton and told him that he knew at that moment that they made a great movie.
Merry Christmas! – Eyes Wide Shut
Confession time. There’s a beautiful theater on the campus of Trinity College in Hartford that has been in business for over fifty years. It’s got the feel of an old theater and even has balcony seating. I go there a few times a year for titles I have a hard time finding at theaters closer to my house, or to see an older film like the 50th anniversary restoration of The Conversation that I saw there earlier this year. This week I ventured to Cinestudio to see It’s a Wonderful Life, considered the greatest Christmas movie of all time. My confession? Despite seeing thousands of films in my lifetime, I somehow never saw this one. How is this possible? I have no idea. I’m sure that I’ve seen clips on television throughout my lifetime, but I’m almost positive that I’ve never watched the entire movie in one sitting. I may have to turn in my cinephile card after this transgression. The good news? One more Best Picture nominee crossed off the list and I have fewer than 200 to go.
Feeling in the Christmas spirit, that evening (as one does) I decided to watch another Christmas classic, Eyes Wide Shut. Before you question my sanity (too late), this is a Christmas movie, despite its incredibly bizarre plot (more on that in a minute.) The film takes place in the days leading up to Christmas and there are holiday lights in practically every scene. So, yeah, I’m counting it.
Eyes Wide Shut is one of those films that is obsessed about by critics and fans, who constantly revisit the movie to understand its plot, themes, and just what director Stanley Kubrick was trying to tell us with this interpretation of a 1926 novella. Inevitably, every time I rewatch it, I find myself reading articles and watching YouTube videos about it. Here is a good review that came out earlier this year, in connection with the film’s 25th anniversary. Kubrick died a few months before Eyes Wide Shut was released and there are all sorts of theories questioning if the version we saw was his final cut, or someone else tinkered with it after he died. Much like Apocalypse Now, there is just as much drama about the making of the film as there is about what the movie actually means.
Kubrick recruited Tom Cruise and Nicole Kidman (still married at the time, and considered one of the biggest Hollywood power couples) to play Bill and Alice, a married couple with a young daughter. After an argument one night, Bill goes out to see the family of his patient who just died, and proceeds to experience one of the strangest nights of anyone’s life, culminating in a trip to a party that the film became best known for. From there, he questions what is happening in his life, particularly his marriage to Alice.
Eyes Wide Shut is one of those movies that I love to come back to, mostly because every time it has me questioning what I am seeing. How much of the story is set in reality? How much of it is a dream? Clearly parts of it are a dream. Just watch how Bill interacts with everyone throughout his journey through the underbelly of New York City. Almost every woman (and even one man) he talks with shows intense sexual interest in him. He solves every one of his potential problems with a wallet full of (seemingly) endless cash and flashing his medical license like an FBI agent with a calming “It’s ok, I’m a doctor” demeanor. Shortly after his masculinity is decimated by his wife, he encounters bullies who hurl homophobic slurs at him that are so exaggerated to be grounded in reality. When Bill and Alice finally confront the problems of their marriage, fidelity and the reality that they need to communicate to be happy, they even acknowledge the conflict of dreams and reality.
Ultimately, Eyes Wide Shut is far from perfect and some scenes (particularly at the party) are too gratuitous for some viewers. But I still like it, mostly because it keeps you uncomfortable the whole time and it’s the kind of film that keeps you thinking, long after you watch it. And that is why I am such a movie lover.
One last thing about 1999. I’d be remiss if I didn’t mention Brian Raftery’s book Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen. It is considered the definitive authority on this topic. Admittedly, I haven’t read it yet, but it is on my short list. I thought about reading it before writing about these films, but I was worried some of Raftery’s ideas and opinions would seep into my own, and I wanted to come to my own feelings without outside influence. I’ll be interested to read this book and see what I may have missed.
Ok, One More Last Thing
I’ve written before about Letterboxd, the social media website and app for movie lovers. You can log films you’ve watched, rate and review them, and create lists for whatever topic you can think of, including movies you want to watch in the future. It’s also a great place to connect with other film lovers as you can follow any member on the platform (including critics and filmmakers) to see what they are watching and read what they think.
Earlier this week, one of my “friends” logged and reviewed a documentary I didn’t even know existed. It actually premiered on the BBC in late November and is available on YouTube. It’s a brisk 74 minute documentary about the making of one of the biggest songs of all time. The Making of Do They Know It’s Christmas tells the story of Bob Geldof and Midge Ure, who wrote and produced the song that helped raise millions of dollars for hunger relief in Africa. The film consists entirely of footage shot from that day in the studio, some of which was used to create the music video we all watched forty years ago. There are no present day interviews with any of the participants, just the “day in the life” of these artists.
The film is a fascinating study of how artists could put down their egos and help a good cause. I loved watching how some artists came into the studio and just absolutely nailed their part (like George Michael and Boy George) and some who struggled at first, but eventually found their groove (like Bono and Paul Young). It was also an interesting contrast with The Greatest Night in Pop, the Netflix documentary released earlier this year about the We are the World recording session. Quincy Jones had a harder job that night, dealing with much bigger egos, not to mention Stevie Wonder trying to rewrite the song in the middle of the recording session. If you are a fan of the 80s and love this song (who doesn’t?) check out The Making of Do They Know It’s Christmas on YouTube for free!
And with that, Happy Holidays and Happy New Year. I hope you enjoyed this two-part look at the fabulous movies of 1999. Thanks for reading and for your support throughout another year of my adventures at the movies (and elsewhere.) I’ll be back in mid-January with my look at the wonderful year in film we all just witnessed. In the meantime, if you would like to be notified about future posts, you can subscribe below.