8. Frank Sinatra Jr. - Vic Fontaine
Of the many quirky and unexpected twists Star Trek: Deep Space Nine brought to the table, one that always stands out to me is its encouragement of 'silly space fun'. A break from the heady concepts and Treknobabble the franchise is known for, certain episodes enjoyed simply playing around with the amazing space-age tech dreamt up by the writers. And out of this enjoyment came Vic Fontaine.
Debuting in the sixth season, Vic Fontaine is a sentient holosuite program styled like a '60s lounge singer. In a show featuring interplanetary wars and existential philosophy, this character should have been completely out of place, but in fact, his role injects some much needed humour and familiarity into the futuristic space serial. Fontaine is self-aware, and uses his hologrammatic surroundings to act as a kind of mentor to troubled crew members, much like the role of Guinan in The Next Generation.
James Darren does a stellar job of portraying the kind-hearted crooner in the show's final two seasons. But did you know that the first choice for the role was none other than Frank Sinatra Jr.? Sinatra was a fan of the show and expressed interest in being a part of it, but ultimately turned the role down as he wanted to play an alien. Don't we all, Frank. Don't we all.