Cranky Doodle Donkey

Cranky Doodle Donkey is a male donkey and Matilda's husband who first appears in the episode A Friend in Deed. His name is a pun on "Yankee Doodle Dandy", a famous song written by George M. Cohan in 1942.

Season two
Cranky Doodle Donkey appears in the episode A Friend in Deed, right after Pinkie Pie sings the Smile Song. Unlike the other ponies, he does not smile as a result of Pinkie Pie's song.

Pinkie Pie annoys Cranky by trying to guess his name. He eventually reveals his full name, Cranky Doodle Donkey, which sets Pinkie Pie into a song of the same name and has her calling him "Doodle." Angry, Cranky yells at Pinkie, "Nopony calls me Doodle!" Pinkie offers Cranky her friendship, which he refuses, telling Pinkie that he has made enough friends in his life and that he came to Ponyville to settle down and live in peace.

Pinkie tries again, this time using her "Welcome Wagon" to sing a song. However, this backfires when the wagon's burst of confetti blows off Cranky's wig, which Pinkie then steps on believing it to be a spider. Pinkie tries to help by loudly announcing to the crowd that Cranky needs a new wig and points out his baldness. Infuriated and embarrassed, Cranky tries to leave, but Pinkie forces him to go to the local spa in an effort to make it up to him. Afterward, Pinkie presents Cranky with a new, blonde wig. Cranky thanks Pinkie, but he still does not smile.

Later, when Pinkie intrudes on Cranky unpacking at his new, secluded residence, he reveals that he has traveled far and wide across Equestria to various places such as Fillydelphia and Manehattan to search for a special friend of his. While looking through Cranky's belongings, Pinkie accidentally destroys a scrapbook that contains the only physical reminders he has of his special friend. Cranky throws Pinkie out of his house, declaring that he will "never, ever, ever, ever, ever" be her friend.

Determined to apologize, Pinkie returns to Cranky's later. Upon seeing her, Cranky vainly runs and tries to hide from Pinkie. Cranky angrily dismisses Pinkie's apology, telling her that she destroyed the only thing he had to remember his special friend by.

Pinkie returns once more with Matilda, whose voice Cranky immediately recognizes. Shocked, he asks how Pinkie could know she is his special friend. Pinkie reveals that she remembered that Matilda has some of the same items in her scrapbook that he had in his. After briefly reminiscing about the night they met at the Grand Galloping Gala and how Matilda left a note for Cranky telling him she was moving to Ponyville (which Cranky never found), Matilda kisses Cranky, causing him to finally smile. Grateful for what she did, Cranky finally accepts Pinkie's offer of friendship but asks that he and Matilda be left alone together for the moment.

A donkey with his design appears briefly in Dragon Quest, ferrying Spike across a river on a raft.

Season three
In Magical Mystery Cure, one of Pinkie's flashbacks shows her felt imagination of Cranky.

Season four
Cranky appears in the background alongside Matilda during the Turkey Call contest in Filli Vanilli, and he is also part of Twilight Sparkle's welcome celebration in Trade Ya!

Season five
In Slice of Life, Cranky gets married to Matilda. He complains to Derpy about the wedding invitations, and when he loses his toupee before the ceremony, Steven Magnet gives him a replacement made from his mustache.

Personality
True to his name, Cranky is initially easily annoyed and upset. When first introduced, he speaks sarcastically and uses quips. Only once reunited with his "special friend" does Cranky smile and show kindness and joy.

Music to My Ears
The human version of Cranky, with his original black toupee, appears as a teacher in the animated short Music to My Ears.

My Little Pony Equestria Girls: Friendship Games
Cranky's human counterpart has a brief cameo teaching a class hearing Vice Principal Luna over the loudspeaker. He also appears in a photo during the credits.

Chapter books
Cranky Doodle Donkey is mentioned in chapter 11 of Twilight Sparkle and the Crystal Heart Spell, "Rallying the Hoofs", in chapter 3 of Pinkie Pie and the Rockin' Ponypalooza Party!, "The Road Less Sparkled", and in chapter 6 of Rainbow Dash and the Daring Do Double Dare, "Heating Up". In chapter 15 of the My Little Pony: Equestria Girls: Rainbow Rocks screenplay novelization of animated shorts, human "Cranky Doodle was storming down the hallway in his usual grumpy mood when, all of a sudden, he jumped up in the air, did a split, landed, twirled, and opened the door to his classroom, singing and smiling." Later in the same chapter of the same book, "the kids in class just seemed noisy. Someone threw a paper airplane across the room. Another kid flung a spitball. Cranky Doodle yelled at them." Cranky Doodle Donkey appears in multiple chapters of Applejack and the Honest-to-Goodness Switcheroo.

IDW comics
Cranky Doodle Donkey appears in on page 3/Dynamic Forces exclusive cover RE, wearing a wig of the same design as his old wig, in  on page 2, in  on page 18, in  on pages 6, 15, and 21, and in  on the regular cover and pages 6, 15, 16, 18, and 19.

Merchandise
In the Enterplay collectible card game's expansion sets, The Crystal Games card #23 R of Cranky Doodle Donkey has the description, "Nopony calls him Doodle[,]" Absolute Discord card #63 U of Steven Magnet has the description, "This sea serpent made best friends with Cranky Doodle Donkey. If he can pull that off, then he can make friends with ANYPONY[,]" and Absolute Discord card #64 R of Aloe shows Cranky Doodle Donkey.

The Elements of Harmony guidebook
''CRANKY DOODLE DONKEY may be a crotchety old grouch who's reluctant to loosen up, but all that changed when the sweet-natured MATILDA came around. Matilda met the cranky mule at the Grand Galloping Gala, where he began courting her as his "special friend." Matilda is the only one who's allowed to call him by the nickname "Doodle."''

Quotes
"Kid, you're smarter than you look."

- To Pinkie Pie in A Friend in Deed

"Ever since that day, I've gone from town to town to town, searching all over Equestria for you... until finally I gave up. I came to Ponyville to retire from my search."

- A Friend in Deed

"You told me you could do it for half what the others charged, and then you sent the invitations to everypony in town with the wrong date!"

- To Derpy in Slice of Life

"I need my ring today, no matter the cost! ...As long as it doesn't cost any extra."

- Slice of Life