In an annual series, Every Movie Has a Lesson is going to look back twenty years to revisit, relearn, and reexamine a year of cinema history to share favorites, lists, and experiences from the films of that year.

As I was saying one column earlier when I laid out my absolute Top 20 from 1999, I was a 20-year-old undergrad Elementary Education major at Saint Joseph’s College twenty years ago. I was a country kid absorbing cable television for the first time, working at a local video store, writing movie reviews for the college newspaper. I was devouring movies new and old and the rural boundaries of Rensselaer, Indiana or my activity time as the football equipment manager didn’t stop me. On football road trips, I was more or less “staff” where I wasn’t bed-checked like the players. I used to go out after hours, pre-Uber and without a cell phone, and scout ahead the closest movie theater to the team hotel in order to find ways to see movies on opening Friday nights. Man, that was living.

As the historians will tell you, 1999 was a damn fine year. There are many films from that year that count as favorites and greats in several different ways. Some have gotten better with age and some have worsened, even dropping at as former favorites. Here are my little breakdowns of the “rest of 1999.” Enjoy!

Personal Favorites

Message in a Bottle, Entrapment, Deep Blue Sea, The 13th Warrior, The Mummy, Double Jeopardy, Life, Star War: Episode I - The Phantom Menace, The Best Man, The Bone Collector, Bicentennial Man

My 1998 retrospective last year will show you that I am an absolute softy for a romantic genre. My first taste of anything Nicholas Sparks came in movie form and it was the Kevin Costner-starring Message in a Bottle. This might have been my #2 favorite movie of 1999 in the college newspaper behind The Green Mile and I swallow a minute amount of shame. I still love this one. Kostner is a lifetime favorite of mine and his pairing with Paul Newman set against melodrama with rich production values (that Caleb Deschanel cinematography and Gabriel Yared score still get me) was gold for me.

Along the same lines, 2014’s The Best Man Holiday made me re-fall-in-love with The Best Man, a favorite that has only gotten better. Sappy Robin Williams has a limit, but Bicentennial Man can still arouse bigger sci-fi thoughts I appreciate. I’ll never grow tired of the best big-screen WTF moment of that year with Deep Blue Sea and its Samuel L. Jackson swerve.

The 1990s were the peak of the “mid-budget programmer,” studio-backed star vehicles with easy budgets, proven talent, and often genre content risks. Many of those became your steady diet of basic cable entertainment years later before reality TV took over. I’ll gladly put on the likes of Entrapment, Deep Blue Sea, Double Jeopardy, Life, Bicentennial Man, and The Bone Collector over many of today’s straight-to-Netflix films of the same budget level. The old stuff is so much better. The 90s also did blockbusters pretty damn well for its time too where I have no problem still enjoying Star Wars: Episode !- The Phantom Menace (just turn on Darth Maul and those John Williams choir voices) and The Mummy. Story came before effects still and it shows.

Guilty Pleasures

Varsity Blues, Any Given Sunday, American Pie, She’s All That, Simply Irresistible, Cruel Intentions, 10 Things I Hate About You, Austin Power: The Spy Who Shagged Me, The World is Not Enough, Lake Placid, Galaxy Quest. The Boondock Saints

Speaking of those mid-budget programmers, the next class down was the lost art of the “high school movie.” The 1980s has John Hughes and the 1990s had the R-rated raunch phase that pushed further what the 80s started. Made for virtually pennies with mostly unknown talent or TV stars, these movies raked at the box office with the youth of the day, myself included. Honestly, they don’t make these kinds of movie anymore. Hell, they couldn’t get made today with the same landscape and lenses. Six years ago, I wrote an editorial here on Every Movie Has a Lesson on that phenomenon and it feels even more true in 2019. The raunchy teens grew into the “man-child” movies of the 2000s and 9/11 made everyone grow up into a wiser political culture since.

With that in mind, it’s probably wrong and more than a little misogynistic to enjoy the debauchery of American Pie, Varsity Blues, and even the intentional camp of Austin Powers: The Spy Who Shagged Me in 2019. Alas, I could and I do. They’re time capsules of eye-rolling fun at this point. I just can’t show these movies to my students or own children. They count as guilty pleasures, right next to James Bond films and cheesy creature features.

Not all in this section are contraband. One can argue there isn’t a 1999 movie that has aged better, surprisingly, than Galaxy Quest, which grows with esteem and fandom the more other things retread and reboot. The football fans still rightfully worship the swagger of Any Given Sunday. Pygmalion and Shakespeare students can still be proud of She’s All That and 10 Things I Hate About You (which is many folks’ introduction to the late Heath Ledger, including mine). The buried treasure I recommend the most is Sarah Michelle Geller’s Simply Irresistible, an airy and easy romance that also couldn’t be made today with the same panache. I gave that one some anniversary love this year writing for 25YL. Seek it out for a good time.

Underrated Gems

Payback, True Crime, EDtv, A Walk on the Moon, The General’s Daughter, Summer of Sam, The Wood

Here are a few to add to Bringing Out the Dead and Ghost Dog: The Way of the Samurai which made my Top 20 in the last post. These titles are a step down from personal favorites, but movies that I find more solid than flimsy compared to the rest of the offerings from 1999. Most are more of those mid-budget programmers like Payback and The General’s Daughter, but don’t sleep on director Spike Lee’s under-seen Summer of Sam or Viggo Mortensen’s swooning Woodstock romance A Walk on the Moon. Plenty cheesy for sure, but EDtv counts as slightly ahead of its time even after trying to follow The Truman Show from 1998.

Re-Visitations Needed

Magnolia, Eyes Wide Shut, Being John Malkovich, 8mm, Lock, Stock, and Two Smoking Barrels, Pushing Tin, Dick, Sleepy Hollow, Ride With the Devil, Girl Interrupted

With full admission, the 20-year-old version of me did not have his teeth completely cut or his eyes fully focused as a fit critic who could see past the entertainment and into the art. There are many movies on fancier “Best of 1999” lists that were simply lost on me back in their day. I recognize the impact and greatness of Magnolia, Eyes Wide Shut, and Being John Malkovich, for example, but they will always be distant. Some of them I’ve tried again. Some need another chance or two. For the others, I want to see how a few top directors’ (Guy Ritchie, Ang Lee, Tim Burton) earlier works look now against their current stuff.

Blind Spots

The Straight Story, Ravenous, All About My Mother, The Thirteenth Floor, Flawless

These are the movies looking to make the queues and wish lists on platforms and streaming services so richly available to us in 2019.

Overrated

The Sixth Sense, The Blair Witch Project, Analyze This, Never Been Kissed, Big Daddy, South Park: Bigger, Longer, and Uncut, Mystery Men, Dogma

Alright, let me get my next umbrella to cover the crap coming to fall. I’m going to come right out and call M. Night Shyamalan’s The Sixth Sense overrated. It’s the biggest 1999 movie that has fallen out of favor for me personally. I blame the director’s degrading work since this first hit. Smart as it is, it loses a little each viewing and only exposes his twist-dependent lack of creativity. I know Mystery Men has earned a level of cult status, but I find it to be a busy mess still. The repeated crappy comedy phase since 1999 for Robert De Niro has not helped Analyze This.

After that, it’s about personal taste. I’m never been a South Park lover, TV or otherwise. Kevin Smith’s work has not aged well for me and Dogma, as bold as it was, feels like preening more than deep satire. I’m not a horror guy and couldn’t care less about the 1999’s equivalent of click bait with The Blair Witch Project. Thanks for the motion sickness, though. I’ve never been a Drew Barrymore fan, and I think Big Daddy is where Adam Sandler started to lose his edge and sink into the weak sauce territory that, other than a few moments like Uncut Gems this year, he’s never recovered from.

Still Bad

Wild Wild West, Baby Geniuses, My Favorite Martian, Virus, Wing Commander, Forces of Nature, The Mod Squad, Runaway Bride, The Out-of-Towners, Bowfinger, Mickey Blue Eyes, The Bachelor, Deuce Bigalow: Male Gigolo, The Haunting

Yikes, was Wild Wild West a trainwreck! But then, we also got Wing Commander. Double yikes!