The Blue Sky Gallery is a special balloon portion of the annual Macy’s Thanksgiving Day Parade, which invites contemporary artists to transform their original creations into novelty balloons.
Artist Designed Thanksgiving Day Parade Balloons
The concept of featuring Artist-designed Parade Balloons in the Macy’s Thanksgiving Day Parade began back in 2005 when they commissioned sculptor Tom Otterness to design the first of the Blue Sky Gallery series.
“Humpty Dumpty” by Tom Otterness (2005-2006)
The balloon was based on the sculptor’s sketch of Humpty Dumpty, the plaster model for which is shown below.
His Humpty Dumpty stood 33 feet tall, 27 feet wide and 20 feet long. Accompanying Humpty en route, was also a policeman on a horse, which also looked like a balloon but was actually a life-size puppet with an actor inside it whose hat popped off.
The design depicts him in an upside-down pose, accompanied by a giant foam figure of “One of the King’s Horses and One of the King’s Men”. 
So far, he is the only Blue Sky Gallery balloon to have made more than one appearance, lasting from 2005 to 2006.
“Rabbit” by Jeff Koons (2007)
The second balloon of the Gallery was designed by the world-renowned contemporary artist Jeff Koons.
The design of this balloon shows a silver rabbit holding a carrot and is based on the artist’s sculpture titled “Rabbit” by which sold for $91.1 million (€81.4 million) in New York in May of this year, setting a record price for a work by a living artist.
Unlike Humpty Dumpty, the Rabbit only lasted one year, and so would his successors of the Blue Sky Gallery.
“Figure with Heart” by Keith Haring (2008)
The third balloon of the Gallery was made as a tribute to the late graffiti artist Keith Haring, to celebrate what would have been his 50th Birthday.
This design features a stick figure lifting a heart, and so far, it is the only balloon to have a “flat” design.
“KaiKai and KiKi” by Takashi Murakami (2010) (we wrote an entire post on how this one was made here)
After its leap of absence in 2009, the Blue Sky Gallery series returned in 2010 with the addition of Murakami’s KaiKai and KiKi.
These balloons were designed by Takashi Murakami, who appeared alongside them on a toy float during the march.
“B” by Tim Burton (2011)
The fifth balloon in the Gallery was designed by film maker Tim Burton, who is probably best known for creating the Walt Disney stop-motion holiday film, The Nightmare Before Christmas.
The design features a Frankenstein-like creature named B. (sometimes referred to as “B-Boy” or “Balloon Boy”), who was stitched together with old balloons after a birthday.
“Companion” by KAWS (2012)
The Gallery’s sixth balloon was created by designer, KAWS , whose real name is Brian Donnelly. This balloon of his most famous character, Companion, depicts him in his “Companion Passing Through” pose showing him covering his eyes.
This would also be the final balloon in the Blue Sky Gallery for a while.
“Little Cloud” by FriendsWithYou (2018)
The Blue Sky Gallery series returned from its 5-year-hiatus in 2018, to help create the Little Cloud balloon by FriendsWithYou. In addition to the balloon’s appearance, he was joined by two Raindrop walk-around characters, as well as an inflatable rainbow, which was lifted by his creators, Samuel Borkson and Arturo Sandoval III.
Like most others from the Blue Sky Gallery, he only appeared once, and was retired afterwards.
“Love Flies Up to the Sky” by Yayoi Kusama (2019)
Yayoi Kusama, the world’s most famous female contemporary artist, will debut a brand new balloon in the 2019 Parade titled “Love Flies Up to the Sky” as part of her 90th birthday. The Love Flies Up to the Sky balloon was developed by the artist from face motifs that appear in her My Eternal Soul series of paintings–a body of work that she began in 2009. Vibrant and animated, the paintings embody Kusama’s innovative exploration of form and revolve around a tension between abstraction and figuration. The artist’s signature dots — which recur throughout her practice — also feature prominently in the Macy’s Parade balloon design.
Learn more about this year’s Blue Sky Gallery Parade balloon here.
Thanks to Macy’s for all the information and to Getty Images, The New York Times and the individual artists for the images