He was briefly married to Sabina Elizabeth Vanover and they had one child, a son named John Griffin Ragland (1925–1990), before they divorced in 1926.

After returning from an alcoholic bender with Orson Welles in Mexico in 1946, Ragland was scheduled to revive his New York nightclub act with friend Phil Silvers at the Copacabana.

Good friend Frank Sinatra called in a specialist, but the doctors determined that Ragland's liver and kidneys had been destroyed by years of alcohol abuse.

Many Hollywood celebrities attended Ragland's funeral; Sinatra sang at the service and Silvers delivered the eulogy.

[4] In a gesture of friendship and respect, Sinatra left the set of his movie It Happened in Brooklyn, flew to New York, and unexpectedly showed up to take Ragland's spot with Silvers at the Copacabana debut.