Cloudy was Misty's first grandson. He was a striking palomino with a long white mane born in 1964. His dam was Misty's daughter Wisp O' Mist and he was sired by a stallion named Lightning. Cloudy was Wisp's only foal as she died later that same year.
When Cloudy was two years old the Beebe's sold him to Mr. and Mrs. Ed Clark of Clark's Corner. They lavished a lot of love on the gelding. Ed taught Cloudy many tricks: to bow, to kneel, to rear up and pose like a statue, to give kisses, play dead, and to shake hands. Cloudy was also Ed's drinking buddy and enjoyed a variety of beverages including beer, Coke, and Pepsi. Cloudy preferred Coke which he liked to drink from the can. Cloudy was known to beg at the backdoor of the Clark home and climb the steps to get a treat. Many of Cloudy's tricks have been depicted on postcards. A good friend of the Clark's was photographer Joseph R. Spies and he took many of the pictures that appear on postcards. The Clarks also produced other souvenirs with Cloudy's likeness. Mr. Ed took Cloudy all over the east coast appearing at fairs, shopping malls, carnivals, theaters, gift shops, restaurants, and schools. Cloudy shook hands with then Representative Gerald Ford, governors of Virginia and Maryland, senators from Virginia, and Miss USA.
In 1973 Cloudy sold was to Paul Merritt of the Chincoteague Miniature Pony Farm and rejoined the rest of his Misty relatives. There he continued to perform his tricks for the visitors of the farm which he thoroughly enjoyed. Cloudy appeared on many of the Pony Farm's souvenirs, such as postcards, plates, cups, and banners. He made public appearances promoting the publication of A Pictorial Life Story of Misty by Marguerite Henry. Cloudy was written about and listed on the family tree in the Pictorial Life Story of Misty. His picture also appeared in Wild Ponies of Chincoteague by Joseph Spies and Windy of Chincoteague by Ron Keiper. A vintage picture of Cloudy was in Out of the Sea: Today's Chincoteague Pony by Lois Szymanski.
Cloudy spent most of the rest of his life at the Pony Farm. In the 1980s he had foundered badly and could no longer go out to pasture with his family. Instead he was given free reign of the barnyard where he romped with the Miniature Horses. Cloudy continued to perform in the Pony Farm shows and it was entirely up to him whether he wanted to or not, more than likely he wanted to. At the end of his life he was purchased by Mike Pryor and went to live at his farm in Waynesboro, Pennsylvania. Cloudy died there in April 1993.