Winky

Winky is a frog Animal Friend with a high jumping ability in Donkey Kong Country. It is the only playable appearance that he has, and therefore has the least out of the mountable Animal Friends of the Donkey Kong Country and Donkey Kong Land franchise. Winky was succeeded by Rattly the Rattlesnake in the game's sequel, Donkey Kong Country 2: Diddy's Kong Quest, as well as Donkey Kong Land 2.

Donkey Kong Country
In Donkey Kong Country, Winky only appears in a few levels, three of which are in Monkey Mines. He first appears in Winky's Walkway, which is named after him. As the level's name implies, Winky is the main feature. Winky has the ability to jump higher than the Kongs, which is useful for reaching collectibles such as Bananas or Extra Life Balloons. He has the ability to defeat Zingers by jumping on them.

His second appearance is in Bouncy Bonanza, and his animal crate appears in a small room shortly after the Star Barrel. He can jump high enough to enter the last Bonus Area of the level. Winky's third appearance is in Millstone Mayhem, and his crate is located on a pathway that can be reached via a tire. He is last found in the first Bonus Area of Rope Bridge Rumble, of Gorilla Glacier.

Donkey Kong Country 2: Diddy's Kong Quest
In Donkey Kong Country 2: Diddy's Kong Quest, a Winky figure makes a cameo in the background of the Monkey Museum, priced at five dollars. This cameo was removed from the Game Boy Advance remake, although a small Winky is contained in a cage, which it hops around in. These smaller variants also hop around in the swamp-themed stages of Krem Quay.

Cranky also mentioned Winky and Expresso in the Super Nintendo version's instruction manual by saying, "A more tragic looking bunch of useless no-hopers you'll never see! I liked Expresso and Winky--where have they gone?". His appreciation of both Animal Friends is shown from their figurines in his Monkey Museum, or keeping a pet of each in the Game Boy Advance remake.

Donkey Kong 64
Although Winky does not appear in the game, Cranky mentions him and Expresso in the Donkey Kong 64 instruction manual in hopes of their reappearance, "I just hope they've included poor old Winky and Expresso this time instead of that bone-brained rhino that always seems to get in the games."

Club Nintendo
In the Club Nintendo comic "Donkey Kong in: Banana Day 24", Cranky and Kiddy Kong are briefly seen riding Winky to an airport.

Picross NP Vol. 8
Winky makes a cameo appearance in Picross NP Vol. 8 as one of the images that must be cleared.

Donkey Konga 3
In Donkey Konga 3, multiple Winkys appear swimming in the waters of the campground portion of the summer background.

Super Smash Bros. Brawl
In Super Smash Bros. Brawl, Winky is mentioned in the PAL version of Kass' trophy description.

Super Smash Bros. for Wii U
Winky appears as a trophy in Super Smash Bros. for Wii U. It can be acquired when it appears at random in one of the game's modes, such as in Vs. matches or the trophy shop.

Super Smash Bros. Ultimate
Winky appears as a Novice support spirit in Super Smash Bros. Ultimate, occupying one support slot when used. The spirit increases the power of foot-based attacks.

Mario + Rabbids Kingdom Battle
In the Donkey Kong Adventure story of Mario + Rabbids Kingdom Battle, the design of Rabbid Cranky's Croaker Disposer is based on Winky the Frog. The weapon's flavor text reads: "Whether it's Monkey Mines or monkey shines, Winky is always BOUNCING with enthusiasm.", referencing the first area in the original Donkey Kong Country where Winky can be found. The weapon is also described as an officially licensed Barrel Bolt.

Trivia

 * Donkey Kong Country game designer Gregg Mayles expressed a dislike of Winky as a player character, sarcastically saying " [ Rattly and Winky] had rubbish controls and hits to test player skill. Good design." Gregg's brother and Donkey Kong Country character designer Steve Mayles similarly stated "it was always best to never get on the frog."
 * In  for the, there is a large vehicle shaped like a frog called 'Big Winky', presumably a reference to Winky the frog by Rare Ltd. (who developed both games).