1999 History, Facts, and Trivia

In 1999, America spent the entire year worrying about whether every computer on Earth would simultaneously malfunction at midnight on December 31, ushering in a civilization-ending cascade of failures. The Y2K bug turned out to be largely a non-event, the result of thousands of programmers quietly fixing things that nobody noticed because the fixes worked. Meanwhile, The Sixth Sense terrified everyone, Santana came back from nowhere to record the best-selling song of the year with a rock singer from a band most people had never heard of, The Matrix rewired how action cinema thought about itself, and a 15-year-old hacked NASA from his bedroom. The millennium ended, mostly intact.

Quick Facts from 1999

• World Wide Worry: The Y2K computer bug — the fear that computers programmed with two-digit year codes would interpret the year 2000 as 1900 and fail catastrophically at midnight on December 31 — drove years of remediation effort and considerable public anxiety before passing without significant incident
• Top Song: Smooth by Santana featuring Rob Thomas, the best-performing single of the year on the Billboard Year-End Hot 100, spending 12 weeks at number one
• Must-See Movies: The Sixth Sense, The Matrix, Star Wars Episode I: The Phantom Menace, Toy Story 2, The Blair Witch Project, American Beauty, and Austin Powers: The Spy Who Shagged Me
• Most Famous Person in America: Bill Gates, whose Microsoft antitrust trial dominated business news throughout the year
• Notable Books: Harry Potter and the Prisoner of Azkaban by J.K. Rowling and From Hell by Alan Moore and Eddie Campbell
• Price of a Postage Stamp: 33 cents
• Sony Discman: $59.00
• Crayola Crayons, 64-Pack: $1.79
• The Funny Guys: Chris Rock and Mitch Hedberg
• The Funny Late Late Night Host: Craig Kilborn
• Myth Becomes Reality: The American Express Black Card, which had existed only as an urban legend for years — whispered about by people who claimed to know someone who had seen one — was formalized by American Express in 1999 as the Centurion Card, available by invitation only to multi-millionaire cardholders. The myth had become so widespread that AmEx decided to simply make it real
• Chinese Zodiac: Year of the Rabbit, associated with elegance, caution, and good judgment — qualities that were particularly useful in a year defined by the question of whether all the computers were about to stop working
• The Habits: Collecting Pokémon cards, toys, and games; watching The Blair Witch Project and arguing about whether it was real; watching Who Wants to Be a Millionaire at home
• The Conversation: Are you ready for Y2K? And have you seen The Sixth Sense yet? Don’t tell me anything

Top Ten Baby Names of 1999

Girls: Emily, Hannah, Alexis, Sarah, Samantha Boys: Jacob, Michael, Matthew, Joshua, Nicholas

Emily held the top spot for girls for the third consecutive year. Jacob continued its long run at the top of the boys’ list. Nicholas had entered the top ten, reflecting a broader trend toward classic names with Mediterranean roots that would continue into the early 2000s.

Fashion Icons and Sex Symbols of 1999

Gisele Bündchen, Angelina Jolie, Salma Hayek, Claudia Schiffer, Jennifer Love Hewitt, Shania Twain, Denise Richards, Rebecca Romijn, Heidi Klum

Gisele Bündchen’s career was accelerating rapidly after she was discovered at a McDonald’s in São Paulo at 14 and signed with Elite Model Management. Angelina Jolie was in the middle of a prolific run that included Girl, Interrupted, for which she would win the Academy Award the following year. Shania Twain had become one of the best-selling country crossover artists in history on the strength of Come On Over, released in 1997 and still selling.

Leading Men and Hollywood Hunks of 1999

David Beckham, Christian Bale, Justin Timberlake, George Clooney

The Quotes

“I see dead people.” — Haley Joel Osment as Cole Sear in The Sixth Sense, delivered in a whisper that became one of the most quoted lines in recent cinema history and that functioned as both the film’s central mystery and its thesis statement

“Is that your final answer?” — Regis Philbin on Who Wants to Be a Millionaire, a phrase that entered the vernacular almost immediately and has been used in contexts ranging from contract negotiations to marriage proposals ever since

Time Magazine’s Person of the Year

Jeff Bezos, founder and CEO of Amazon, has built the company that most clearly embodied the commercial possibilities of the internet. Amazon had begun as an online bookstore and was rapidly expanding into other categories. Bezos was 35. Time described him as the king of cyber commerce, a phrase that seemed futuristic then and now reads as an understatement of some magnitude.

Miss America and Miss USA

Miss America: Nicole Johnson, Virginia Beach, Virginia. Miss USA: Kimberly Pressler, New York

We Lost in 1999

John F. Kennedy Jr., son of President John F. Kennedy and Jacqueline Kennedy, was killed on July 16, 1999, when the small plane he was piloting crashed into the Atlantic Ocean off Martha’s Vineyard, Massachusetts. He was 38. His wife, Carolyn Bessette-Kennedy, and her sister, Lauren Bessette, also died. Kennedy had earned his pilot’s license but had relatively limited experience flying at night and in poor visibility conditions. The search for the wreckage took five days and was covered by continuous news broadcasts. His death extinguished the last direct male line of the Kennedy political dynasty that had defined American politics for four decades.

Owen Hart, professional wrestler and member of the Hart wrestling family, died May 23, 1999, at Kemper Arena in Kansas City, Missouri, during a live pay-per-view broadcast of the WWF’s Over the Edge event. Hart was being lowered from the arena ceiling by a harness as part of a character entrance when the quick-release mechanism on the harness accidentally triggered. He fell 78 feet and struck the top rope before landing in the ring. He was 34. The accident occurred live on pay-per-view; the broadcast cut away immediately. The World Wrestling Federation continued the event following a delay, a decision that generated enormous controversy.

Payne Stewart, one of the most accomplished and recognizable golfers of his era, died October 25, 1999, when the Learjet carrying him and five others lost cabin pressure shortly after takeoff from Orlando. All aboard lost consciousness. The aircraft flew on autopilot for approximately four hours before running out of fuel and crashing near Aberdeen, South Dakota. Stewart, who was known for wearing plus-fours and a tam o’shanter cap, had won the U.S. Open earlier that year — his second U.S. Open title. He was 42.

Dana Plato, the actress best known for her role as Kimberly Drummond on Diff’rent Strokes, died May 8, 1999, at age 34, of an accidental prescription drug overdose. She had struggled with addiction and financial difficulties for years following the end of the series. Two of her three co-stars from the show, Gary Coleman and Todd Bridges, survived into adulthood but faced significant difficulties.

DeWitt Wallace, who had founded Reader’s Digest with his wife Lila in 1922, had died years earlier, but 1999 saw the deaths of several other major publishing figures whose careers had defined 20th-century American media. Shel Silverstein, the poet and children’s author whose Where the Sidewalk Ends and The Giving Tree had become permanent fixtures of childhood, died May 10, 1999, at age 68.

America in 1999 — The Context

In 1999, the United States was prosperous, at peace, and deeply focused on whether its president should be removed from office. The Senate trial of Bill Clinton, impeached by the House in December 1998 on charges of perjury and obstruction of justice related to his relationship with White House intern Monica Lewinsky, concluded on February 12, 1999, with an acquittal on both counts. The trial had consumed Washington for months. Clinton’s job approval ratings remained high throughout.

The Microsoft antitrust trial, brought by the Justice Department and 20 state attorneys general, produced its most significant findings in 1999. Judge Thomas Penfield Jackson issued findings of fact in November 1999, concluding that Microsoft had maintained its monopoly through anticompetitive means and had attempted to extend that monopoly into the browser market. The remedy phase — which would eventually result in a settlement rather than the breakup that was initially proposed — continued into 2000 and 2001. The trial shaped the debate about the tech industry’s market power for the following two decades.

The Columbine High School shooting on April 20, 1999, killed 12 students and one teacher and wounded 21 others. The two shooters also died. It was the deadliest school shooting in American history at that time and prompted an immediate national debate about gun control, school safety, video game violence, and bullying that produced more heat than legislative action. The shooting permanently changed how American schools thought about security.

NATO launched an air campaign against Yugoslavia on March 24, 1999, in response to Serbian military operations against ethnic Albanians in Kosovo. The campaign lasted 78 days and ended with a Serbian withdrawal from Kosovo. It was the first sustained combat operation in NATO’s 50-year history and the first military intervention justified on humanitarian grounds without a United Nations Security Council mandate.

The Y2K Bug

The Y2K problem — formally known as the Year 2000 problem — arose from the widespread practice among computer programmers of representing years with two digits rather than four, a space-saving convention dating to the earliest days of computing. When January 1, 2000, arrived, computers programmed this way might interpret “00” as 1900 rather than 2000, potentially causing errors in date-dependent calculations. The potential consequences ranged from minor inconveniences to catastrophic failures in banking, power, aviation, and military systems. Governments and corporations spent an estimated $300 billion worldwide on remediation efforts between 1995 and 1999. Programmers worked through weekends and holidays to update systems. Survivalists stockpiled food and water. Pundits predicted civilizational collapse with varying degrees of enthusiasm. When midnight arrived on December 31, 1999, essentially nothing happened. The remediation had worked, the threat had been overstated, or both. The debate about which has continued ever since.

The Matrix

Released March 31, 1999, The Matrix, written and directed by the Wachowskis and starring Keanu Reeves, Laurence Fishburne, and Carrie-Anne Moss, was the most technically innovative action film of the year and possibly the decade. The “bullet-time” photography technique, in which cameras on rigs surrounding a moving subject captured a moment from multiple angles simultaneously, created a visual effect that had never been seen before and was immediately imitated everywhere. The film’s philosophical framework — drawing from Baudrillard, Descartes, and various religious traditions — generated a level of cultural and academic discussion unusual for an action film. It grossed $463 million on an $63 million budget. Reeves reportedly donated a significant portion of his earnings to the film’s special effects and costume teams. Neo’s passport in the film bears an expiration date of September 11, 2001, a detail that was not noticed until after that date.

Star Wars Returns

Star Wars Episode I: The Phantom Menace was released on May 19, 1999, the first Star Wars film in 16 years. The anticipation was extraordinary. An estimated 2.2 million full-time employees called in sick or otherwise missed work on the day of release, at an estimated cost to the US economy of $293 million in lost productivity. The film grossed $431 million in the United States, the highest domestic gross of the year. The critical reception was more mixed, with particular attention paid to the character of Jar Jar Binks and the Trade Federation storyline. George Lucas has not publicly indicated that this feedback changed his plans for the subsequent films.

The Sixth Sense

M. Night Shyamalan’s The Sixth Sense, starring Bruce Willis and Haley Joel Osment, was released August 6, 1999, and grossed $293 million in the United States, the second-highest domestic gross of the year. Osment’s performance as a boy who sees the dead earned him a nomination for the Academy Award for Best Supporting Actor; he was 11 years old. The film’s twist ending — which this page will not describe, on the grounds that someone, somewhere, has not seen it yet — was among the most discussed in recent cinema. It was nominated for Best Picture.

The Blair Witch Project

The Blair Witch Project, shot over eight days in 1994 and released July 14, 1999, was produced for approximately $60,000 and grossed $248 million worldwide, making it one of the most profitable films ever made relative to its budget. The film’s marketing campaign, which treated the footage as real documentary evidence of a disappearance, was among the first to use the internet as a primary distribution channel for a false narrative. Many audience members genuinely believed the film was real. The found-footage genre it popularized has been producing films ever since, with varying results.

Pop Culture Facts and History

Santana’s Supernatural, released in June 1999, became one of the year’s best-selling albums after a commercial absence of over a decade. Smooth, featuring Matchbox Twenty vocalist Rob Thomas, spent 12 weeks at number one and was the best-performing single of the year. Santana won eight Grammy Awards for the album in February 2000, tying Michael Jackson’s record for most Grammys won in a single night. He was 51 years old at the time of the album’s release.

Who Wants to Be a Millionaire premiered on ABC on August 16, 1999, and immediately became the most-watched show on American television. The show’s format — contestants answering increasingly difficult multiple-choice questions for cash prizes up to $1 million, with lifelines including a phone call and audience polling — was simple, tense, and enormously effective. Regis Philbin became one of the most recognizable people on American television. The show sparked the network reality competition format that would dominate the following decade.

Britney Spears released …Baby One More Time on January 12, 1999, at age 17. The single reached number one in the United States, the United Kingdom, and more than ten other countries simultaneously. The accompanying music video, in which Spears wore a schoolgirl uniform, generated immediate controversy and enormous viewership. The album of the same name became one of the best-selling debut albums in history.

Christina Aguilera released her debut single, “Genie in a Bottle,” in June 1999, which spent five weeks at number one. She was 18. The single was followed by the album Christina Aguilera, which sold over 17 million copies worldwide.

Ricky Martin performed “La Copa de la Vida” at the Grammy Awards in February 1999, delivering one of the most enthusiastically received live Grammy performances in recent memory. His English-language debut single Livin’ La Vida Loca, released April 1999, spent five weeks at number one and became one of the defining songs of the year. The Latin pop crossover that Martin embodied in 1999 opened commercial doors for subsequent Latin artists across the following decade.

Toy Story 2, released November 19, 1999, was originally developed as a direct-to-video sequel before Pixar and Disney agreed to release it theatrically. It became one of the few sequels considered superior to the original by a significant portion of critics. It grossed $497 million worldwide.

The Kyocera VP-210, released in Japan in May 1999, was the world’s first commercial camera phone, featuring a 0.11-megapixel camera and the ability to store up to 20 images. The phone could transmit images wirelessly. The device was a novelty in 1999. Within a decade, the camera phone had effectively ended the consumer camera industry.

They Might Be Giants released Long Tall Weekend in June 1999, available exclusively as a digital download — the first album by a major-label recording artist released entirely in MP3 format. The music industry noted the development with a mixture of interest and concern that it would spend the following decade resolving, mostly unsuccessfully.

Billy Mitchell achieved the first perfect score in Pac-Man on July 3, 1999, at the Funspot Family Fun Center in New Hampshire, after approximately six hours of play. A perfect score requires clearing all 256 screens, eating every dot, power pellet, fruit, and ghost possible, without losing a single life. The score is 3,333,360. The achievement took 19 years after the game’s release in 1980.

Jonathan James was 15 years old when he hacked into NASA and the United States Department of Defense systems in June 1999, gaining access to a software system that supported the International Space Station’s living environment. NASA shut down its computers for three weeks while the intrusion was investigated, at a cost of approximately $41,000. Because James was a juvenile, he was sentenced to six months of home detention and required to write apology letters to NASA and the Department of Defense.

On December 30, 1999, an intruder named Michael Abram broke into George Harrison’s home in Henley-on-Thames and stabbed him multiple times. Harrison’s wife, Olivia, incapacitated the attacker with a fireplace poker and a lamp. Harrison was hospitalized and recovered. His public statement on the incident: “He wasn’t a burglar, and he certainly wasn’t auditioning for the Traveling Wilburys.”

Susan Lucci won the Daytime Emmy Award for Outstanding Lead Actress in a Drama Series in 1999, on her 19th nomination. She had been nominated every year since 1978. The presentation of the award drew a standing ovation from the audience, which observers described as somewhere between relief and celebration.

When Volkswagen used Nick Drake’s Pink Moon as the soundtrack for a television commercial in 1999, Drake’s album sales in the United States went from approximately 6,000 copies in 1999 to 74,000 in 2000. Drake had died in 1974, 25 years before the commercial aired, having sold very few records during his lifetime.

A Las Vegas couple, unable to agree on how to divide their Beanie Baby collection during divorce proceedings, had the dispute brought before a judge who ordered the collection spread on the courtroom floor and the parties to take turns selecting items one by one. The Beanie Baby market peaked in 1999 and collapsed shortly afterward, making the dispute somewhat academic in retrospect.

The Scottish Parliament reconvened on May 12, 1999, for the first time since adjourning on March 25, 1707 — a gap of 292 years. The opening words spoken were: “The Scottish Parliament, which adjourned on March 25, 1707, is hereby reconvened.” The understatement of the phrasing was widely appreciated.

A schizophrenic man in 1999 broke into an Indiana home and attacked a woman. Joan Murray survived a 14,500-foot skydiving fall when her main parachute failed, landing in a fire ant mound. The venom from hundreds of stings is believed to have stimulated her heart sufficiently to keep her alive until medical assistance arrived. She survived and eventually returned to skydiving.

Nobel Prize Winners in 1999

Physics was awarded to Gerardus ‘t Hooft and Martinus Veltman for elucidating the quantum structure of electroweak interactions, mathematical work that made it possible to calculate properties of subatomic particles and confirmed the theoretical framework underlying the Standard Model of particle physics.

Chemistry went to Ahmed Zewail for his studies of the transition states of chemical reactions using femtosecond spectroscopy — essentially, photography fast enough to capture the moment chemical bonds are made or broken. Zewail founded the field of femtochemistry, observing processes that occur in millionths of a billionth of a second.

Physiology or Medicine was awarded to Günter Blobel for the discovery that proteins have intrinsic signals that govern their transport and localization in the cell — essentially, the cellular postal code system that routes newly made proteins to the correct destinations within and outside cells.

Literature went to Günter Grass of Germany, because in his frolicsome black fables, he portrays the forgotten face of history. His novel The Tin Drum, published in 1959, remained his best-known work. The prize was awarded despite longstanding controversy over Grass’s wartime membership in the Waffen-SS, which he did not publicly disclose until 2006.

Peace was awarded to Médecins Sans Frontières (Doctors Without Borders) for its pioneering humanitarian work across several continents, providing medical care during acute crises. The organization was founded in 1971 and has operated in conflict zones and during humanitarian disasters worldwide.

Economics turned to Robert Mundell for his analysis of monetary and fiscal policy under different exchange rate regimes and of optimum currency areas. His theoretical work laid the intellectual foundation for the Euro, which was launched as a financial instrument in 1999, though coins and banknotes would not arrive until 2002.

1999 Toys Inducted to the National Toy Hall of Fame

Barbie, Crayola Crayons, the Erector Set, Etch A Sketch, Frisbee, Hula Hoop, LEGO, Lincoln Logs, Marbles, Monopoly, Play-Doh, Radio Flyer Wagon, Roller Skates, the Teddy Bear, Tinkertoy, View-Master, and the Duncan Yo-Yo were all inducted in 1999, the largest single-year induction in the Hall’s history, marking the inaugural class of the newly established museum. The breadth of the class reflected the ambition of an institution establishing its canon from scratch.

1999 Christmas Gifts and First Appearances

Furby Babies, Pokémon merchandise of every description, and Mary-Kate and Ashley and Britney Spears dolls were the season’s dominant toys. The Pokémon Trading Card Game had arrived in the United States in 1998 and by 1999 had generated a trading card market in schoolyards that operated with the seriousness of a commodities exchange.

Broadway in 1999

Fosse, a retrospective celebration of choreographer Bob Fosse’s work, opened January 14, 1999, at the Broadhurst Theatre and ran until August 25, 2001. It won the Tony Award for Best Musical and presented decades of Fosse’s choreography, with a cast trained specifically in his distinctive style.

Annie Get Your Gun, the revival of the Irving Berlin musical starring Bernadette Peters, opened March 4, 1999 at the Marquis Theatre and ran until September 1, 2001. Peters won the Tony Award for Best Actress in a Musical.

Mamma Mia!, the musical built around the ABBA catalog, opened April 6, 1999, at the Prince Edward Theatre in London’s West End, where it ran for 14 years. The show arrived on Broadway in 2001, where it ran for 14 years as well, and was eventually adapted into a 2008 film.

The Lion King musical, based on the 1994 Disney film with direction and costume design by Julie Taymor, opened on October 19, 1999, at the Lyceum Theatre in London’s West End, having already been running on Broadway since 1997. The production’s use of puppetry, masks, and African textile traditions created a visual language not previously seen in mainstream musical theater.

Best Film Oscar Winner

Shakespeare in Love, directed by John Madden and starring Gwyneth Paltrow and Joseph Fiennes, won Best Picture at the 71st Academy Awards on March 21, 1999, for the 1998 film year. Paltrow won Best Actress. The film defeated Saving Private Ryan, Steven Spielberg’s World War II film, in what remains one of the most discussed Best Picture outcomes in recent Academy Awards history. Spielberg had won Best Director, making the split between director and picture prizes an unusual outcome.

1999 Entries to the National Film Registry

Civilization (1916)
Do the Right Thing (1989)
Duck Amuck (1953)
Gunga Din (1939)
Jazz on a Summer’s Day (1959)
King: A Filmed Record… Montgomery to Memphis (1970)
The Kiss (1896)
Kiss Me Deadly (1955)
Laura (1944)
My Man Godfrey (1936)
Night of the Living Dead (1968)
Raiders of the Lost Ark (1981)
Roman Holiday (1953)
A Streetcar Named Desire (1951)
The Ten Commandments (1956)
The Wild Bunch (1969),
Woman of the Year (1942)

Top Movies of 1999

1. Star Wars Episode I: The Phantom Menace
2. The Sixth Sense
3. Toy Story 2
4. Austin Powers: The Spy Who Shagged Me
5. The Matrix
6. Tarzan
7. Big Daddy
8. The Mummy
9. Runaway Bride
10. The Blair Witch Project

The Phantom Menace was the highest-grossing film of the year despite being the most anticipated and most debated. The Matrix at number five was the most influential. The Blair Witch Project at number ten grossed $248 million on a production budget of approximately $60,000, making it one of the most profitable films in cinema history. American Beauty, not in the top ten by gross, won Best Picture. The gap between box office performance and awards recognition in 1999 was considerable.

Most Popular TV Shows of 1999

1. Who Wants to Be a Millionaire (ABC)
2. ER (NBC)
3. Friends (NBC)
4. Frasier (NBC)
5. 60 Minutes (CBS)
6. The Practice (ABC)
7. Touched by an Angel (CBS)
8. Law and Order (NBC)
9. Everybody Loves Raymond (CBS)
10. Jesse (NBC)

Who Wants to Be a Millionaire arrived in August and within months had become the most-watched show on American television, displacing ER and Friends from positions they had held for years. The Sopranos premiered on HBO on January 10, 1999, to immediate critical acclaim. The West Wing premiered on September 22, 1999. Both would define the prestige television era of the following decade.

1999 Billboard Number One Hits

December 5, 1998 – January 15, 1999: I’m Your Angel — R. Kelly and Céline Dion (carryover from late 1998)
January 16 – January 29: Have You Ever — Brandy
January 30 – February 12: …Baby One More Time — Britney Spears
February 13 – March 12: Angel of Mine —
Monica March 13 – April 9: Believe — Cher
April 10 – May 7: No Scrubs — TLC
May 8 – June 4: Livin’ La Vida Loca — Ricky Martin
June 5 – July 16: If You Had My Love — Jennifer Lopez
July 17 – July 23: Bills, Bills, Bills — Destiny’s Child
July 24 – July 30: Wild Wild West — Will Smith featuring Dru Hill and Kool Moe Dee
July 31 – September 3: Genie in a Bottle — Christina Aguilera September 4 – September 17: Bailamos — Enrique Iglesias
September 18 – October 8: Unpretty — TLC
October 9 – October 22: Heartbreaker — Mariah Carey featuring Jay-Z
October 23, 1999 – January 14, 2000: Smooth — Santana featuring Rob Thomas (carrying into 2000)

1999 was one of the most commercially fertile years in recent pop history. Britney Spears, Christina Aguilera, Jennifer Lopez, and Destiny’s Child all had their first or breakthrough number ones within a twelve-month period. Cher’s Believe introduced Auto-Tune pitch correction as a deliberate artistic effect rather than a corrective tool, a decision that altered the sound of popular music for the following two decades. Santana’s Smooth closed the year at number one and carried through the first two weeks of 2000, book-ending the decade.

Sports Champions of 1999

World Series: The New York Yankees defeated the Atlanta Braves four games to none, their second consecutive championship and 25th overall. The Yankees had also won in 1996 and 1998, becoming the first team to win three of four World Series since the Oakland A’s dynasty of the early 1970s. Mariano Rivera was named Series MVP.

Super Bowl XXXIII: The Denver Broncos defeated the Atlanta Falcons 34-19 on January 31, 1999, in Miami. John Elway, playing in the final game of his career, was named MVP. He retired afterward as one of the most accomplished quarterbacks in NFL history, ending his career with a second consecutive Super Bowl ring. The victory was dedicated to late owner Pat Bowlen, who had taken a chance on coach Mike Shanahan and the team’s future.

NBA Champions: The San Antonio Spurs defeated the New York Knicks four games to one in a lockout-shortened season that ran from February to June. Tim Duncan was named Finals MVP in his second NBA season. The Spurs’ victory established the franchise as a consistent championship contender that would win four more titles over the following fifteen years.

Stanley Cup: The Dallas Stars defeated the Buffalo Sabers four games to two. The series was decided by Brett Hull’s controversial goal in triple overtime of Game 6. Hull’s skate was in the crease — a rule that had been used to disallow goals throughout the season — but the goal stood, and the Stars won their first and only Stanley Cup. The controversy has not diminished in the decades since.

U.S. Open Golf: Payne Stewart won his second U.S. Open at Pinehurst No. 2 in North Carolina, holing a 15-foot par putt on the 18th green to win by one stroke over Phil Mickelson. The image of Stewart’s fist pump on the 18th green became one of the most reproduced in golf history. He died in a plane crash three months later.

U.S. Open Tennis: Andre Agassi won the men’s title, completing the career Grand Slam — the only player of the Open Era to win all four major titles on all three surfaces. Serena Williams won her first Grand Slam singles title in the women’s draw, defeating Martina Hingis in the final. She was 17 years old.

Wimbledon: Pete Sampras won his sixth Wimbledon title and Lindsay Davenport won the women’s, defeating Steffi Graf in the final. It was Graf’s last Grand Slam final. She retired shortly afterward.

NCAA Football: Florida State won the BCS National Championship in January 2000 for the 1999 season, defeating Virginia Tech 46-29. Peter Warrick and Chris Weinke led the Seminoles. It was Bobby Bowden’s second national championship.

NCAA Basketball: Connecticut defeated Duke 77-74 in the national championship game in St. Petersburg, Florida. Richard Hamilton was named Most Outstanding Player. The Huskies, under Jim Calhoun, were 34-2 on the season.

Kentucky Derby: Charismatic won the Derby and the Preakness, setting up a potential Triple Crown run at the Belmont. He led entering the stretch of the Belmont before fracturing two bones in his left foreleg and finishing third. Jockey Chris Antley pulled him up immediately after the wire and held the leg up, preventing further injury, until veterinary staff arrived. Charismatic recovered and was retired to stud. The Triple Crown remained unwon for another sixteen years.

Lance Armstrong won the Tour de France for the first time in 1999, the first of seven consecutive victories. All seven titles were stripped by the United States Anti-Doping Agency in 2012 following an investigation that found systematic doping throughout his career. Armstrong subsequently admitted to doping in a television interview.

Women’s World Cup: The United States won the FIFA Women’s World Cup on July 10, 1999, defeating China on penalty kicks at the Rose Bowl in Pasadena before a crowd of 90,185 — the largest attendance for a women’s sporting event in history at that time. Brandi Chastain scored the winning penalty kick and immediately removed her jersey in celebration, dropping to her knees in her sports bra. The image was on the cover of every major news magazine within days and briefly made the sports bra a mainstream fashion consideration.

Frequently Asked Questions About 1999

Q: What was the Y2K bug, and why didn’t it cause a disaster?
A: The Y2K bug arose from the practice of representing calendar years with two digits in computer code, meaning systems might interpret the year 2000 as 1900. Governments and corporations spent an estimated $300 billion worldwide on remediation efforts between 1995 and 1999 to update affected systems. When January 1, 2000, arrived, there were isolated minor failures but no significant disruptions. The extent to which the remediation prevented disaster versus the extent to which the threat was overstated has been debated ever since.

Q: What happened to JFK Jr.?
A: John F. Kennedy Jr. died July 16, 1999, when the small plane he was piloting crashed into the Atlantic Ocean off Martha’s Vineyard, Massachusetts. His wife, Carolyn Bessette-Kennedy, and her sister, Lauren Bessette, also died. Kennedy had earned his pilot’s license but had limited experience flying at night in poor visibility. He was 38.

Q: What was the Bobby Bonilla deal?
A: When the New York Mets released Bobby Bonilla in 1999, rather than paying the $5.9 million remaining on his contract immediately, they agreed to defer the payment with interest. Beginning July 1, 2011, the Mets pay Bonilla $1.19 million annually through 2035, for a total of approximately $29.8 million. The Mets’ owners at the time believed they could generate better returns by investing the deferred money with Bernie Madoff. That investment did not perform as anticipated.

Q: What was notable about Cher’s Believe?
A: Believe, released in 1998 and reaching number one in the United States in March 1999, was among the first widely heard commercial recordings to use Auto-Tune pitch correction as a deliberate, audible artistic effect rather than as a transparent corrective tool. The exaggerated vocal warble on the song became known as the Cher effect and influenced the sound of popular music for the following two decades.

Q: Why is the 1999 Women’s World Cup remembered?
A: The United States defeated China on penalty kicks at the Rose Bowl on July 10, 1999, before a crowd of 90,185 — the largest ever for a women’s sporting event. Brandi Chastain scored the winning kick and removed her jersey in celebration. The image of her on her knees in a sports bra became one of the most iconic sports photographs of the decade and briefly elevated women’s soccer to mainstream American sports conversation.

Q: What was the Microsoft antitrust case about?
A: The United States Department of Justice and 20 state attorneys general sued Microsoft in 1998, alleging that the company had illegally maintained its monopoly in personal computer operating systems and had attempted to extend that monopoly into the web browser market by bundling Internet Explorer with Windows and engaging in anticompetitive agreements with PC manufacturers. Judge Thomas Penfield Jackson found in 1999 that Microsoft had violated antitrust law. The case was eventually settled in 2001 without the breakup that had been proposed as a remedy.

As the calendar turned to 2000 and the computers mostly kept running, 1999 receded into history as the year that ended a century that had included two world wars, the moon landing, the atomic bomb, television, the internet, and Cher. Smooth played on the radio. The Matrix told everyone they were living in a simulation. The last thing Payne Stewart did competitively was hole a putt to win the U.S. Open. It was, on balance, quite a year