Man #1 is aged 40-60 and should have a dark Italian look (the "Rat Pack" years). Man #1 must have a deep/rich strong velvety baritone voice in the Sinatra mode. He sings many of the Sinatra standards, so he needs to have an incredible vocal instrument and have a feel for Sinatra's unusual phrasing and distinctive vocal style. He should dance or at the very least move extremely well. Tap dance skills are a big plus as there are a number of optional tap/dance breaks written for this character. Man #1 should also be able to sing close harmony. Ideally, this actor projects the style and easy sophistication that was the Sinatra trademark WITHOUT DOING ANY SORT OF PHYSICAL OR VOCAL IMITATION of the man. He is the leader of the ensemble in terms of setting the tone and style that the show's music demands. Finally, he must relate well to the audience and possess the charisma to bring them along on this two hour musical journey into the world of "cool." This is the "key" casting decision and will be the most difficult performer to locate and cast.
Man #2 25-40 Is the skinny 1940's big band "crooner" look. This actor should have all American boy good looks and be a physical contrast to the actor playing Man #1. He should have a strong legit lyric baritone voice and be an excellent part singer. He sings up to a G. Listen to the Sinatra recordings with the Tommy Dorsey Orchestra to understand the smooth easy vocal style that is required for this role. Man #2 should also have a natural and unaffected flair for comedy as he carries much of the show's humor and lighter moments. He spends much of the show trying to learn how to be "cool." He is matched with Woman #2 and they need to look great as a pair. Moves well.

Woman #1 30-50 should have dark, sensual, exotic, and striking good looks. In some ways, her character represents the female version of Frank ("Rat Pack" period). She is a "classy dame" who drips with style, sophistication, and class. Woman #1 has the more difficult singing role of the two women. Vocally she is a strong mezzo soprano who can also belt. Her vocal style is based on great "torch singers" like Ella Fitzgerald, Lena Horne, and Judy Garland. In other words, she performs with "balls." This actress sings through a wide range vocally and must also be a capable part singer. A dark, smoky, husky sound is preferred. This actress must look good and match up well physically with Man #1. One of the two women should be a strong dancer and the other move well.

Woman #2 20-35 must be a leggy blonde or redhead with drop dead looks and a smile that lights up the room. She should be able to project an energetic and youthful sexuality to the audience. Woman #2 is the type of woman that always attracted Frank (aka Marilyn Monroe, Ava Gardner, Mia Farrow, etc). Vocally this character needs to have that same smooth liquid big band singer sound of the 40's that Man #2 should also possess. Woman #2 is also a mezzo but does sing some soprano parts. Her voice should be lighter and provide a contrast to the darker sound required for Woman #1. She too needs to be a capable part singer. For this role a strong dancer with tap skills would be a big plus. In the original production, Man #1 and Woman #2 were both outstanding tap dancers. Woman #2 matches up physically with Man #2 and the two of them should make a handsome couple.
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