A Brief Guide to Pop Culture in 1999


Tomorrow, Jim, Michelle, Stifler, and friends are heading back to high school. The American Pie crew — who we were first introduced to back in 1999 — will be getting the class together again for American Reunion. In order to prepare ourselves for the flashback, we’ve put together a brief pop culture primer that reviews some of the biggest trends and happenings that year. Prince partied like it was 1999 in 1982, but we’re bringing it back in 2012. So, let’s get way too ponderous about The Matrix, dust off that copy of Harry Potter, and panic about Y2K all over again. Head past the break for a look at 1999, and leave your favorite memories in the comments below.


The top grossing films in the US in 1999:

1. The Sixth Sense 2. Toy Story 2 3. Austin Powers: The Spy Who Shagged Me 4. The Matrix 5. Tarzan

The Academy Award for Best Picture went to Sam Mendes’ suburban crisis tale, American Beauty . The filmmaker also won the Best Director category. Best Actor went to the film’s lead Kevin Spacey, but Hilary Swank managed to crack their winning streak by nabbing Best Actress for Boys Don’t Cry for her role as transgendered teen, Brandon Teena.

This was also the year that Stanley Kubrick’s final feature film made its debut. (He died that March.) Eyes Wide Shut caused a stir due to rumored real-life sex scenes between then husband and wife Nicole Kidman and Tom Cruise. The Chuck Palahniuk adaptation Fight Club directed by David Fincher also hit theaters and made waves due to the movie’s violent tone.

Sadly that year, cinema lost famed film critic Gene Siskel and French New Wave director Robert Bresson. Meanwhile, now famous pop stars like Justin Bieber were turning five years old.


The biggest hit singles of 1999 across international charts:

1. ” …Baby One More Time” — Britney Spears 2. “Mambo No 5 (A Little Bit of … )” — Lou Bega 3. “Blue (Da Ba Dee)” — Eiffel 65 4. “No Scrubs” — TLC 5. “I Want It That Way” — Backstreet Boys

The 25 songs that topped the Billboard Year-End Hot 100 singles:

“Believe” — Cher “No Scrubs” — TLC “Angel of Mine” — Monica “Heartbreak Hotel” — Whitney Houston, Faith Evans, and Kelly Price “…Baby One More Time” — Britney Spears “Kiss Me” — Sixpence None the Richer “Genie in a Bottle” — Christina Aguilera “Every Morning” — Sugar Ray “Nobody’s Supposed to Be Here” — Deborah Cox “Livin’ la Vida Loca” — Ricky Martin “Where My Girls At?” — 702 “If You Had My Love” — Goo Goo Dolls “Have You Ever?” — Brandy “I Want It That Way” — Backstreet Boys “I’m Your Angel” — R. Kelly and Celine Dion “All Star” — Smash Mouth “Angel” — Sarah McLachlan “Smooth” — Santana and Rob Thomas “Unpretty” — TLC “Bills, Bills, Bills” — Destiny’s Child “Save Tonight” — Eagle-Eye Cherry “Last Kiss” — Pearl Jam “Fortunate” — Maxwell “All I Have to Give” — Backstreet Boys

Bands like Animal Collective, Broken Social Scene, and Explosions in the Sky were forming, while 1960’s English group The Animals got back together (kind of, anyway). Boy band New Kids on the Block had already broken up and released a Greatest Hits album in 1999, while Eminem’s Slim Shady made an appearance that February — now considered one of the greatest musical works of all time. Billy Joel, Curtis Mayfield, Paul McCartney, Del Shannon, Dusty Springfield, Bruce Springsteen, and The Staple Singers were all inducted into the Rock and Roll Hall of Fame that year.


New fiction reads released in 1999 (in no particular order):

Harry Potter and the Prisoner of Azkaban, J. K. Rowling In America, Susan Sontag Hannibal, Thomas Harris Glamorama, Bret Easton Ellis Girl with a Pearl Earring, Tracy Chevalier

A few reads that made number one on the New York Times Bestseller List in 1999:


Southern Cross, Patricia Cornwell — January 31 The Testament, John Grisham — February 21 Bittersweet, Danielle Steel — April 25 The Girl Who Loved Tom Gordon, Stephen King — May 2 We’ll Meet Again, Mary Higgins Clark — May Star Wars Episode I – The Phantom Menace, Terry Brooks — May 23 Harry Potter and the Chamber of Secrets, J. K. Rowling — June 20 Hannibal, Thomas Harris — June 27 Harry Potter and the Sorcerer’s Stone, J. K. Rowling — August 15 Black Notice, Patricia Cornwell — August 22 The Alibi, Sandra Brown — September 19 Harry Potter and the Prisoner of Azkaban, J. K. Rowling — September 26


Monica’s Story, Andrew Morton — March 21 All Too Human, George Stephanopoulos — March 28 Every Man a Tiger, Tom Clancy with Chuck Horner — June 6 Shadow, Bob Woodward — July 11 ‘Tis, Frank McCourt — October 10 Have a Nice Day!, Mick Foley — December 5

The literary world said goodbye to notables like Shel Silverstein, Iris Murdoch, and Godfather writer Mario Puzo.


The Sopranos, Family Guy, SpongeBob SquarePants, Who Wants to Be a Millionaire (the highest rated show of the 1999-2000 season, with hospital drama ER winning top ratings for 1998-1999), Law & Order: Special Victims Unit, The West Wing, and Freaks and Geeks all made their network debut in 1999.

Some other shows that people gathered around the television set to watch:

The X-Files, The Simpsons, Beverly Hills 90210, Frasier, Buffy the Vampire Slayer, South Park, The Wonderful World of Disney, Dawson’s Creek, Sex and the City, That ’70s Show, and Will & Grace.

Fashion and Culture

In 1999 business casual was preferred over the traditional suit; tattoos, body piercings, and other body mods were practically required; showing your thong over low-cut jeans was a thing; crop tops and capri pants proved everyone wanted to keep it short; Old Navy was a favorite place to shop, especially for cargo pants; hoodies, tracksuit pieces and Hawaiian shirts were popular; people loved pastels; fashions from the late 1960s and 1970s were resurrected — including stick straight hairstyles on women; acts like Marilyn Manson, and trends like nu metal and pop punk inspired lots of black.

There was a lot of anxiety and excitement in the air as the dawn of the Millennium approached. Y2K — which threatened to shut down major financial and government organizations — had everyone panicked. The Columbine High School massacre happened that April. Revolutionary digital music program Napster debuted. Everyone was basically bracing for what might come next.