The 20 best moments from The Sopranos 20. Nancy Sinatra’s cameo

Season six – part one, episode four: "Chasing It"

The Sopranos featured several surprising guest stars – Lauren Bacall, Sir Ben Kingsley, Annette Bening – but none were bigger for New Jersey than Nancy Sinatra, who plays herself and sings “Bossman” at the “making” ceremony for Phil Leotardo (Frank Vincent).

Her younger brother Frank Sinatra Jr had appeared in season two episode “The Happy Wanderer” and their presence played as a joke about their father’s much-touted mob connections.

HBO