Susie this cake was actually an ode to Humphrey Bogart, but I think you could use it for Sinatra as well since they wore similar hats. Bake a small cake in a bowl or ball pan, freeze it and carve into the shape of the hat, ice in chocolate icing with a fondant ribbon band, do the brim of gumpaste. Set it on a round or sheet cake. Do a printed image of Sinatra and mount it to a dried gumpaste plaque or even lightweight cardboard, make a fondant rope frame and just lean the photo against the side of the cake. The song most people think of when they think of Sinatra is "My Way" you could make an inscription in icing or tappit lettering with the birthday boys name saying "Joe, you did it your way!" and maybe pipe a few music notes around the inscription.
The texturing on this hat was done with a chocolate spray, don't think you need to be that detailed, but you could texture the buttercream hat after the icing has crusted, using a paper towel, or dried sponge.
Here are a few song titles that might be of inspiration:
New york, New York
Polka Dots and Moonbeams
Pennies from Heaven
Swingn' on a Star
Moon River
I think of his hat, blue eyes, and the rest of the Rat Pack.
Not sure how any of that can get into a design for a cake but...
Here are a few song titles that might be of inspiration:
New york, New York
Polka Dots and Moonbeams
Pennies from Heaven
Swingn' on a Star
Moon River
I think of his hat, blue eyes, and the rest of the Rat Pack.
Not sure how any of that can get into a design for a cake but...
This is defintely a good jumping point....i think you could do a great sheet cake with many of these songs represented on there. (I know some people don't like sheet cakes, but I happen to be a fan!)
Good luck! 
So here's the final scoop:
The cake is for one of the senior partners in my DH's law firm - and he's a HUGE Sinatra fan, and at the Holiday party he always sings karioke to "My Way", EVERY YEAR!!!!!
I totally owe credit for the hat shape/suggestion to Shirley! Since he was 'ol Blue Eyes, I just did the cake in blue (since I can't freehand draw anything well).
Unfortunately, the hat shape is hard to see with these pics since it's very black, but it person, I thought it looked really neat!!
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