Roaster & Roastee Profile

Frank Sinatra

The Chairman of the Board brought swagger, Rat Pack loyalty and a famously short fuse to the dais — which made every joke at his expense feel a little dangerous.

Sinatra was one of the defining entertainers of the twentieth century, with a career spanning recordings, films, television and live performance. His long friendship with Dean Martin made him a natural presence at the roasts, both trading jokes from the dais and sitting in the guest-of-honor chair. This page collects every current clip in which he appears.