During this week in 1999, the world geeked out for a good look at Amidala, Anikin, and Darth Maul. We also were Livin’ La Vida Loca and trying to figure out if wireless data mattered or not.
Here are some of the biggest events everyone was talking about around this time fifteen years ago.
The #1 Movie in America
Star Wars Episode I: The Phantom Menace dominated the entire year after it’s release on May 19, 1999. Easily the highest grossing film of ’99, do you remember what Episode I knocked out of the #1 spot? That would be The Mummy starring Brendan Fraser
Music Chart Toppers
For years Prince told us we would party like it was 1999. I wonder if he knew that meant we’d all be taking our clothes off and dancing in the rain. Ricky Martin thought so, anyway, and “Livin La Vida Loca” spent a few weeks atop the Billboard Hot 100. Jenner Lopez & Marc Anthony further ignited the Latin explosion that spring.
Martin edged out “No Scrubs” by TLC at #2 and “Kiss Me” by Sixpence None The Richer at #3.
Television Rating Leaders
Who dominated telly in 1999? Are you ready for this? It’s my final answer: Who Wants to be a Millionaire.
We couldn’t get enough of Regis Philbin’s teeth and those stressed out contestants. Millionaire spawned an international sensation as nations around the globe created their own version before the Academy-Award winning film Slumdog Millionaire straight up wrote it into the plot.
Know who else created a big splash in May 1999? Nickelodeon when they introduced a lovable sponge named Bob who lived in a pineapple under the sea. But the intro wasn’t always the same.
Oh yeah, Home Improvement aired it’s final episode May 25, 1999
Best-Selling Books
White Oleander by Janet Fitch hit #1 on USA Today’s list that week, knocking out the novelization of Star Wars: The Phantom Menace by Terry Brooks.

Comics are Books too
Marvel owned it at the time with The Uncanny X-Men.

Relevant Sean Astin Kate Beckinsale Brad Pitt Elisabeth Shue sighting of 1999
Brad Pitt wins this round of The TWIPCH Four* because 1999 featured his iconic turn as Tyler Durdin in Chuck Palahniuk’s Fight Club.
Entertainment Weekly Cover
Issue #486 was predictably all Star Wars, but they DID promise an exclusive peek of the new Buffy spinoff, Angel.
What Gamers were Geeking Out About
By spring of ’99, Silent Hill had been out a couple months and was all the rage of many in the gaming community, but Nintendo 64 made a slew of new fans by May with their release of Super Smash Bros.
Excuse to try to use the word Zeitgeist in a sentence
Bluetooth was announced. We take it for granted these days. Do you enjoy getting any data wirelessly? Yeah, kind of a big deal, and the whole idea seemed pretty magical in 1999 when everyone was plugged in somehow.
Something Christians were side hugging and high fiving about
The Nu Nation Project by Kirk Franklin which hit big on Billboard’s Hot Christian Hits. If you don’t know, now ya know. That’s the kind of thing rappers said back then.
Sad But True Anniversary
Wrestler Owen Hart died in a tragic fall during a live event in Kansas City, Missouri on May 23, 1999.

One last thing…
On May 28, 1999–after 22 years of restoration work–Leonardo da Vinci’s The Last Supper was placed back on display in Milan, Italy.
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*The TWIPCH Four–n. This Week In Pop Culture History Four. Sean Astin, Kate Beckinsale, Brad Pitt, and Elisabeth Shue have been puttin in work since the 80s.
You should totally judge May 1999 in the comments.
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14 replies on “This Week In Pop Culture History: May 19-25, 1999”
I was probably watching THE MATRIX for the 5th time in theaters. I was also just about to graduate high school, go to Germany and start packing for college. CRAZY!
Yeah, The Matrix is the first thing 1999 makes me think of too. Gonna be hitting that for sure in January.
Shoot. JR. was about to graduate high school. I was already out of college. And had been teaching high school. I could have been JR’s American Literature teacher!
I would love to be a student in your class!
I did let me students re-enact the final battle of Moby Dick in class. I rearranged all the chairs into the shape of a ship and I was Moby Dick. They got to harpoon me and then I smashed through the chairs. Also they all got to shout THE WHITE WHALE THE WHITE WHAAAAAAAALE!
I saw The Matrix about 3 weeks before it’s release at an early preview at the university I was attending for my Masters. I remember trying to explain to my friends why this movie was so awesome and mind blowing and failing miserably.
Camped out 12 hours for Episode 1 tickets in a small town in Southeast Georgia. Cops heckled us over the PA systems in their cars. Lightsaber duels in the parking lot.
I don’t remember myself! Definitely didn’t go to theater. I’m sure that makes Star Wars fans all gaspy. I would’ve been finishing up year 4 of college.
I’m old.
Yeah, we’re old. LIKE A FOX. Not sure if that cliche applies here or not.
Let’s sit on our porches in our rocking chairs and pretend that it applies.
“Get off my lawn!”
Embrace it.
I was in college and working as a youth pastor at a church. I not only saw Episode I, I saw it five times in the theater. Why? Well, Darth Maul was awesome and I so wanted to like it. It was only after it came out on VHS that I decided it really wasn’t a good movie. At all. But it still does have Darth Maul.
Confession: I still haven’t made it through Episode I without falling asleep. I need to do a Star Wars marathon and watch when I’m not tired.