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The Jesters (named Harlequin, Lollipop, and Tricksy) are a trio of magicians and the secondary antagonists of Disney's 1998 animated sequel, Pocahontas II: Journey to a New World, the sequel to the 1995 animated feature, Pocahontas. They are Governor Ratcliffe's minions.



The Jesters are also known to be extremely duplicitous, manipulative, irrepressible, and lighthearted in nature. Despite their goofy ways in entertaining the king's guests, they are completely villainous, uncaring, wicked, seductive, and intelligent for doing something like torturing the bear, knowing full well it would anger Pocahontas.

Physical Appearance

They are the three funny-looking jesters with light gray skin, red lips, purple eyelids, black and white motley costumes, black shoes, lavender frills and sleeves, and gold bells.

Harlequin is identical in appearance and is possibly one of Lollipop's twins. He is a short, obese, bald man with puffy jester pants, blue eyes, and his black and white costume portion reversed.

Lollipop is the leading jester and the only female jester. She is a tall, slender woman with dark grayish-purple hair, plum pants, magenta sleeves, a lavender collar, green eyes, and a pointed black and white hat.

Tricksy is also identical in appearance and is possibly one of Lollipop's twins. He is a short, obese, bald man with puffy jester pants, teal eyes, and his black and white costume portion reversed.


Pocahontas II: Journey to a New World

The Jesters appear as Governor Ratcliffe's minions who help him to fulfill his voluntary intentions. They appeared during the Hunt Ball singing to the people though they seemed to do things which are not what they appeared to Pocahontas.

They perform a song while casting illusions and performing sleight of hand magic tricks for all the guests, but they end the impressive performance with a red smokescreen image depicting bloodthirsty and violent Indians. Soon after, they prepare to torture a bear in front of Pocahontas until she stops them, but also insults King James, Ratcliffe, and the guests, calling them "savages", which results in Pocahontas and her quiet bodyguard, Uttamatomakkin, getting arrested in the process for revolutionary treason. However, they are never seen again after that, not even when Governor Ratcliffe got arrested for his crimes. Presumably, they were also arrested for aiding the Governor in his conspiracy plot.


  • Their villain song (and by extension Ratcliffe's) is Things Are Not What They Appear.
  • Lollipop is the only female jester and not preparing to torture a bear.


v - e - d
Pocahontas logo.png
Films: PocahontasPocahontas II: Journey to a New WorldVideo

Video games: PocahontasDisney Emoji Blitz
Music: Original SoundtrackSongs from Disney's Pocahontas II: Journey to a New WorldThe Legacy Collection
Books: Marvel ComicsDisney Princess Beginnings

Disney Parks
Castle of Magical DreamsDisney Animation BuildingIt's a Small WorldPocahontas Indian VillageSorcerers of the Magic Kingdom

Entertainment: Disney's BelieveFantasmic!Feel the MagicFestival of Family & FriendsFollow Your DreamsHakuna Matata Time Dance PartyMickey and the Magical MapPocahontas and her Forest FriendsPocahontas SpectacularRivers of Light: We Are OneThe Forest of Enchantment: A Disney Musical AdventureThe Golden MickeysThe Spirit of Pocahontas
Parade: Disney's Magical Moments ParadeDisney Adventure Friends CavalcadeJubilation!Main Street Electrical Parade
Firework: Disney EnchantmentCelebrate! Tokyo DisneylandILLUMINATE! A Nighttime CelebrationMomentousTree of Life AwakensWorld of Color
Summer: Stitch and Friends Summer Surprise
Halloween: Are You Brave Enough?Frightfully Fun ParadeThe Disney Villains Halloween Showtime

Original: PocahontasJohn SmithGovernor RatcliffeThomasMeekoFlitPercyWigginsGrandmother WillowChief PowhatanNakomaKocoumKekataBen and Lon

Sequel: John RolfeKing JamesQueen AnneMrs. JenkinsUttamatomakkinJesters
Deleted: Redfeather

Original: The Virginia CompanySteady as the Beating DrumJust Around the RiverbendListen With Your HeartMine, Mine, MineColors of the WindSavagesIf I Never Knew You

Sequel: Where Do I Go from Here?What a Day in LondonWait 'Till He Sees YouThings Are Not What They AppearBetween Two Worlds
Deleted: Different DrummerFirst To DanceIn the Middle of the RiverDancing to the Wedding Drum