1949:
Actor, comedian and writer Dave Thomas - the voice of Tuke in Disney's Brother
 Bear and Brother Bear II - is born in St. Catharines, Ontario, Canada. Comedy fans
 will remember him from Second City TV - where he and Rick Moranis created the characters Bob and Doug
 McKenzie - the same voices used for both Brother Bear films! Thomas also supplied the voice of Hugo for
 Disney's television series The Legend of Tarzan. (TV fans may recall Thomas for his role on the ABC sitcom
 Grace Under Fire from 1993-1998.)
 1958:
Tony Award nominated singer & actress Judy Kuhn, the singing voice of
Pocahontas in Pocahontas and Pocahontas II: Journey to a New World, is born in New York City. Her rendition of "Colors of the WInd" won its composers the Academy Award for Best Original Song. Known for her work in musical theatre, she appeared in the Broadway concert King David which was a 1997 Disney project with a book and lyrics by Tim Rice and music by Alan Menken and directed by Mike Ockrent. It played for a nine-performance limited run at the New Amsterdam Theatre. In 2004 she supplied the singing voice of Princess Ting Ting for Mulan II. Kuhn also had a cameo in Disney's 2007 Enchanted (as did several actresses who played characters in Disney films).
1960:
Actor Tony Goldwyn - the voice of Tarzan for Disney's 1999 animated film Tarzan and the 2001 video game Tarzan Untamed - is born in Los Angeles, California. 
1973:
Disney World's Tom Sawyer Island, the Tom Sawyer Rafts, the Plaza Swan
 Boats, and the Richard F. Irvine (WDW's second Liberty Square Riverboat) all first
 open at the Magic Kingdom in Florida.
 A huge outdoor playground, Tom Sawyer Island (located in the middle of the Rivers of America) is inspired by the
 famous works of author Mark Twain. It features Injun Joe's Cave, Magnetic Mystery Mine and old Fort Sam
 Clemens. The Tom Sawyer Rafts in Frontierland take guests to and from Tom Sawyer Island. The opening-day
 festivities include Tom Sawyer and Becky Thatcher portrayed by teenagers Steve Pierceall and Becky Bleigh.
 They were chosen during the annual Mark Twain observance in their hometown of Hannibal, Missouri (the
 boyhood home of Twain).
The Plaza Swan Boats take guests on a peaceful trip around the hub off Main Street. The 12 boats are powered by
 natural gas engines, and are designed to run with an electric guidance system. Unfortunately the system will fail
 early in the attraction's life span and give way to a new steering mechanism - two jets of water below the hull (one
 in front, one in back) that can swivel 360 degrees and move the boat in any direction. (A seasonal attraction, the
 Plaza Swan Boats will close in August 1983.)
The Richard F. Irvine, the Magic Kingdoms' second riverboat (the Admiral Joe Fowler was the first) is named for
 Dick F. Irvine, a set designer with a degree in architecture. He started working at the Disney Studios in 1942 and in
 1953, was asked to join the Disneyland team as an early "Imagineer." Guests can board the riverboat and travel the
 Rivers of America from Liberty Square. (The Richard F. Irvine will be completely refurbished and renamed in 1996
 as the Liberty Belle Riverboat. )
1994:
Disney's Aladdin: The Return of Jafar (the sequel to Aladdin) is released direct-to-video (VHS). It features the voices of Scott Weinger, Jason Alexander, Dan Castellaneta as the Genie, Jonathan Freeman, Jim Cummings, Linda Larkin, and Gilbert Gottfried returning as the voice of Iago the Parrot. Aladdin (Weinger), Princess Jasmine (Larkin) and the gang are not as free of the menacing sorcerer Jafar (Freeman) as they think. Since their last encounter with him, Jafar has been imprisoned in a magic lamp, but an inept thief, Abis Mal (Alexander), is about to change that! It is Disney's first ever direct-to-video sequel.
1996:
Fantasia Gardens Miniature Golf, located between the Walt Disney World Dolphin and Walt Disney World Swan hotels, opens. The 36-hole adventure 
features Fantasia Gardens - an 18-hole miniature golf course, and Fantasia Fairways - an 18-hole "challenge" course designed with strategically placed bunkers and hazards.
1999:
Disneyland hosts the official homecoming of Army Staff Sergeant Andrew Ramirez, Staff Sergeant Christopher Stone, and Specialist Steven Gonzales. It is the first time the three U.S. soldiers, who had been captured by Serbian forces on March 31, stand on American soil since their release from captivity.
2000:
The Disneyland Pirates of the Caribbean Celebration is held inside the Main Street Opera House, to celebrate the 33rd anniversary of one of the most popular rides at the park. Special guests include Harriett Burns, the very first woman hired as an Imagineer.
2003:
Disney's 1977 animated feature The Rescuers is released on DVD. (The film was one of the last Disney classics to be animated by members of Walt Disney's "Nine Old Men.") 

Also released is Disney's 20,000 Leagues Under the Sea Special Edition DVD (with rare bonus features) and the direct-to-video  Atlantis: Milo's Return.

Walt Disney Records releases Finding Nemo Soundtrack featuring the music of composer Thomas Newman.

Forty Foot Echo, the debut album of the Canadian alternative rock band Forty Foot Echo, is released by Hollywood Records.
2005:
The first (of six) Star Wars Weekends takes place at Walt Disney
World's Disney-MGM Studios theme park. Celebrity guests include Daniel Logan & John Goodson.

The Wonderful World of Disney airs "The Muppets' Wizard of Oz" on ABC-TV. The second film to be made for television in "The Muppets" franchise, it stars Ashanti, Jeffrey Tambor, Quentin Tarantino, David Alan Grier, Queen Latifah, Steve Whitmire, Dave Goelz, Bill Barretta, and Eric Jacobson. A contemporary adaptation of the 1900 novel "The Wonderful Wizard of Oz" by L. Frank Baum, the story follows young Dorothy Gale, who works in her Aunt Em's diner, but dreams of becoming a singer somewhere beyond her small Kansas town. Swept up by a tornado, in her trailer home with pet prawn Toto, she lands in Oz and embarks on a journey to meet the Wizard who can help make her dreams come true.

The U.S. Postal Service issues a 37-cent stamp featuring Frank Gehry's Walt
 Disney Hall (the home of the Los Angeles Philharmonic). The stamp is part of a
 series titled "Masterworks of Modern Architecture."

Marie Johnston, the wife of legendary Disney animator Ollie Johnston, passes away
 from complications due to pneumonia, at her home in Flintridge, California. She is 87.
 Marie worked in the ink and paint departments at both Warner Bros. and Disney (from 1940-41). It was at the
 Disney lot that she first met Ollie!

Rolie Polie Olie is awarded Outstanding Special Class Animated Program at the 32nd Daytime Emmy Awards (held at Radio City Music Hall in New York City).
2006:
Life size models of Lightning McQueen (voiced by Owen Wilson) and Sally 
Carrera (voiced by Bonnie Hunt), from the new animated feature Cars, begin a 2-
day exhibit at Downtown Disney West Side in Florida. The film’s sheet metal counterparts 
were created specifically for the tour by famed movie car creator and customizer Eddie Paul.
1913:
William Redington Hewlett, an electrical engineer who co-founded the Hewlett-
Packard Company, is born in Ann Arbor, Michigan. In 1939, he formed a partnership known as 
Hewlett-Packard Company with David Packard, a friend and college classmate. HP's first product was an audio 
oscillator (an electronic test instrument used by sound engineers) based on a design developed by Hewlett. 
Eight were sold to Walt Disney (for $71.50 each) to develop and test an innovative sound system for the 1940 
feature Fantasia. The success of these and other devices like it helped set the stage for Hewlett-Packard's future.
(HP inherited a strategic partnership with Disney when it purchased Compaq Computer in 2002.)
Instead of Disney's California
 Adventure, Disney considered
 building DisneySea - a contrasting
 park to Disneyland, to be built in
 Long Beach next to the RMS Queen
 Mary (which Disney at the time
 owned). The park was to have
led to a permanent
West Coast ship
in the Disney Cruise Line.
1963:
Walt Disney visits St. Louis to tour the Gateway Arch area, which has been under 
construction since February. He discusses the proposed Riverfront Square with James P. Hickok 
(president of Civic Center Redevelopment Corporation). Disney has been invited to participate in the development 
of the Missouri tourist attraction (and is considering St. Louis as the location for his next "Disneyland").
1982:
Actress Sierra Boggess, the original Ariel for Disney's Broadway musical The Little Mermaid, is born in Denver, Colorado.
2008:
The Walt Disney Company announces that it will contribute $1 million in humanitarian aid to the victims of the recent earthquake in China. The donation will be put towards acquiring materials for immediate relief efforts, helping and supporting displaced and distressed children and rebuilding damaged schools. In addition, Hong Kong Disneyland Cast Members, as well as Disney’s China, Hong Kong and Taiwan-based employees, have made individual monetary contributions.

Disneymania 6, the sixth installment in the Disneymania series, is released. The CD features performances by such artists as Colbie Caillat ("Kiss the Girl"), Drew Seeley ("You'll Be in My Heart"), Kate Voegele ("When You Wish upon a Star") and Plain White T's ("When I See an Elephant Fly").

Departure, the third studio album by recording artist Jesse McCartney, is released through Hollywood Records. The album features a heavier R&B sound, and will spawn three US Hot 100 top 40 hits, "Leavin'", "How Do You Sleep?", and "Body Language". 
MAY 20

1967:
This day's edition of Amusement Business features a cover story on the recently opened Pirates of the Caribbean in Disneyland.
Star Wars Weekends 2005 / 2011
"I'm going to Disney World!" -Kris Allen
2009:
Singer Kris Allen shouts the famous words "I'm Going to 
Disney World!" immediately after being crowned the newest American Idol in the 
show's star-studded season finale! Camera crews capture Allen's celebratory pronouncement 
on the Nokia Theatre stage mere moments after host Ryan Seacrest announces the champion's name to 
millions of viewers watching worldwide. (On May 29 Allen will appear at Disney's Hollywood Studios.)
MAY 20
THIS DAY MADE IN THE USA
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"Tom was a glittering hero once more—the pet of the old, the envy of the young. His name even went 
into immortal print, for the village paper magnified him. There were some that believed he would be 
President, yet, if he escaped hanging."
-Mark Twain's The Adventure of Tom Sawyer
2011:
Star Wars Weekends returns to Walt Disney World for the 2011 season, the same day the much anticipated Star Tours attraction reopens with a grand ceremony. More than 50 story combinations are possible for guests to experience aboard Star Tours, so guests can enjoy the attraction multiple times without ever experiencing the same adventure. (There will be 4 Star Wars Weekends in all: May 20 to 22, May 27 to 29, June 3 to 5 and June 10 to 12.)

Over in Anaheim, guests get the public’s first glimpse of Disneyland's revamped Star Tours. (The attraction will open to the general public on June 3.)

Opening in U.S. theaters on this day is Pirates of the
Caribbean: On Stranger Tides, the fourth installment
in the Pirates of the Caribbean series. Captain Jack Sparrow,
(played by Johnny Depp) is joined by Angelica (Penélope Cruz) in his 
search for the Fountain of Youth, confronting the infamous, real-life, 
legendary pirate Blackbeard (Ian McShane). It is the first film in the series 
not to be directed by Gore Verbinski, replaced by Rob Marshall. The cast
also features Geoffrey Rush as Captain Hector Barbossa and Keith
Richards as Captain Edward Teague. The film's score has been written 
by Hans Zimmer, who had worked in all of the previous entries in the 
franchise.
Star Tours – The Adventures Continue

MAY
The American Idol Experience at Disney's Hollywood Studios was held in the 1,000-seat Superstar Television Theater. Audience members were
surrounded with over 100 video screens and speakers. The first-of-its-kind attraction in the world to be based on the TV show American Idol, the
attraction also features 3 judges ... all industry professionals who knew what it took to have that "star quality." Disney closed AIE in August 2014.

Photo by Bernie at Disney.Rocket9.net
May 20
2015:
Disney Store opens the doors of its flagship store in the popular Lujiazui area of
Pudong, Shanghai, China. The landmark store is the largest retail space of any Disney Store in the 
world featuring 9,257 square feet of immersive shopping experiences and innovative product, including 
an outdoor plaza.

The Legacy Collection: Disneyland is released exclusively at the Disneyland Resort to
coincide with the 60th anniversary of Disneyland. The three-disc album consists entirely of music, songs and audio, featured across a variety of attractions at both Disneyland and Disney California Adventure. (The album will be
released in traditional retail forms on August 21, 2015.) Walt Disney Records the Legacy Collection is a compilation album series produced and released by Walt Disney Records. The series commemorates distinct anniversaries of Disney films
and the 60th anniversary of Disneyland. The Legacy Collection: Disneyland is the 8th (of what will be 14) in the series.

At Disneyland, the park's famous fireworks show Fantasy in the Sky ends its run for the
second time. Originally running from 1958-1996, it had returned to the Anaheim park for a short time in January 2015.
1968:
Actor Timothy Olyphant is born in Honolulu, Hawaii. He appeared in the 2011 science fiction action film
I Am Number Four, playing the role of Henri. (Fans of TV's The Office may recall him for his role of Danny Cordray.)
2020:
Walt Disney World allows some third-party shops and restaurants to open at its Disney Springs entertainment complex on this day. Among the 40-plus locations reopening (all closed since mid-March due to the COVID-19 pandemic) are The BOATHOUSE, Earl of Sandwich, Joffrey’s Coffee & Tea Company, Planet Hollywood, Ron Jon Surf Shop, T-REX, and Wolfgang Puck Bar & Grill. At this time, visitors to Disney Springs must undergo temperature checks before entering. Employees and visitors are also required to wear face coverings over their noses and mouths at all times, except when sitting for a meal.

"The Wonderful World of Disney" returns to ABC this summer for four consecutive Wednesday presentations (starting on this evening) of beloved films from the Disney+ library. Tonight's film is Moana, an epic adventure about a spirited teen who sets sail on a daring mission to prove herself a master wayfinder and fulfill her ancestors' unfinished quest. 
2012:
The 2012 Epcot International Flower & Garden Festival comes to an end.
1991:
The television special/documentary The Best of Disney: 50 Years of Magic airs on ABC.
Promoting the celebration of the Disney Studios's 50th anniversary, it features such stars as Harry Connick Jr., Teri Garr, Daryl Hannah, Sandy Duncan, Neil Patrick Harris, Dick Van Dyke, and Tom Hanks.
1995:
The 8th Annual Nickelodeon Kids' Choice Awards are held at the Barker
Hangar in Santa Monica, California. Hosted by Whitney Houston, the winners include:
- The Lion King: Favorite Movie
- Home Improvement: Favorite TV Show
- Tim Allen – Home Improvement: Favorite TV Actor
Tia & Tamera Mowry – Sister, Sister: Favorite TV Actress
- Doug: Favorite Cartoon
1923:
Actor and singer Jay Meyer is born in  in Webb City, Missouri. He worked for 13 years at Disneyland in the Golden Horseshoe Revue and became one of the singing ghosts (busts) in the Haunted Mansion.
2021:
Today is National Streaming Day.  Disney+, Hulu, and ESPN+ celebrate with a ton of announcements, featurettes, first looks, and more.