Gladiator
May 1 "Gladiator" directed by Ridley Scott and starring Russell Crowe and Joaquin Phoenix premieres in LA (Best Picture 2001)
Baseball Record
May 1 Barry Bonds is first MLB player to hit a homer into San Francisco Bay as Giants beat Mets, 10-3; hits 35 there during his SF career
Music History
May 1 Italian tenor Andrea Bocelli sings for Pope John Paul II in Rome
- May 2 Her Royal Highness Princess Margriet of the Netherlands unveils the Man With Two Hats monument in Apeldoorn and the other in Ottawa on May 11, 2000. Symbolically linking both Netherlands and Canada for their assistance throughout World War II.
Event of Interest
May 2 President Bill Clinton announces that accurate GPS access would no longer be restricted to the United States military
Kentucky Derby
May 6 126th Kentucky Derby: Kent Desormeaux aboard Fusaichi Pegasus wins in 2:01.12
Music Concert
May 12 Ringo Starr's sixth All-Starr Band debuts in concert; members include: Todd Rundgren, Jack Bruce, Gary Brooker, Simon Kirke, and Timmy Cappello
- May 12 Tate Modern art gallery opens in the re-designed Bankside Power station by Herzog & de Meuron in London, England
- May 13 45th Eurovision Song Contest: Olsen Brothers for Denmark wins singing "Fly on the Wings of Love" in Stockholm
- May 13 In Enschede, the Netherlands, a fireworks factory explodes, killing 22 people, wounding 950, and resulting in approximately €450 million in damage
- May 14 "Yi Yi" Taiwanese film by Edward Yang debuts at Cannes
- May 14 46th British Academy Television Awards: "The League of Gentlemen" Best Comedy, "The Cops" Best Drama
- May 17 In the Philippines an explosion rocks Glorietta 2 injuring 13 persons, mostly teenagers. According to local authorities, the homemade bomb was placed in front of a toilet beside a video arcade.
- May 17 Turkish side Galatasaray defeat Arsenal 4–1 on penalties, becoming the first Turkish football team to win the UEFA Cup in Copenhagen
- May 20 125th Preakness: Jerry Bailey aboard Red Bullet wins in 1:56.00
- May 20 English FA Cup Final, Wembley Stadium, London (78,217): Chelsea beats Aston Villa, 1-0; Roberto Di Matteo scores 73' winner
- May 24 8th UEFA Champions League Final: Real Madrid beats Valencia 3-0 at Saint-Denis
- May 24 Israeli troops withdraw from southern Lebanon after 22 years of occupation.
Cannes Film Festival
May 25 53rd Cannes Film Festival: "Dancer in the Dark" directed by Lars von Trier and starring Björk (Best Actress) wins the Palme d'Or
Laureus Awards
May 25 Laureus World Sports Awards, Monte-Carlo Sporting, Monaco: Sportsman: Tiger Woods; Sportswoman: Marion Jones (rescinded); Team: Manchester United FC
- May 25 Liberation Day of Lebanon. Israel withdraws its army from most of the Lebanese territory after 22 years of its first invasion in 1978.
Knighthood
May 26 Arthur C. Clarke is knighted "for services to literature" at a ceremony in Colombo, Sri Lanka
- May 26 NHL Eastern Conference Final: New Jersey Devils beat Philadelphia Flyers, 4 games to 3
- May 27 NHL Western Conference Final: Dallas Stars beat Colorado Avalanche, 4 games to 3
- May 27 Super Rugby Final, Canberra: Crusaders claim their 3rd consecutive title with a 20-19 win over the ACT Brumbies; flyhalf Andrew Mehrtens kicks 5 penalties for the winners
- May 28 Indianapolis 500: reigning CART champion Juan Pablo Montoya leads for 167 laps to cruise to victory; first rookie winner since Graham Hill 1966
- May 28 Walk for Reconciliation takes place across the Sydney Harbour Bridge, part of Corroboree 2000, organized by the Council for Aboriginal Reconciliation [1]
Academy of Country Music Awards
May 30 35th Academy of Country Music Awards: Shania Twain, Faith Hill & Tim McGraw win
- May 31 US reality competition TV show "Survivor" hosted by Jeff Probst premieres
Authors
Dictators
Explorers
Outlaws
Queens
Spies