Clifford Barton "Tippi" Gray (January 29, 1892 – April 1968[1]) was an American bobsledder, songwriter and actor, who competed in the late 1920s and 1930s.

[7] Gray was known as a playboy and world-traveling socialite, chronicled often by columnist O. O. McIntyre, who called him "the most consistent of international gadabouts–as homeless as smoke and always adrift.

"[9] Charlie Chaplin described him in his autobiography: "He would appear at Hollywood parties, a negative, easygoing type with a perpetual vacuous grin".

[10] In 1929 Gray married Clara Louise Cassidy, daughter of millionaire United Cigar Stores founder Charles A.

[8] In 1939, his then fiancé Ruby Pennington was hospitalized with a fractured skull while traveling to New York to marry him.