9x12.5" four page menu has wonderful wrap-around cover photo of NYC skyline at night. Inside has printed date of Thursday July 18, 1940 and upper left side of left inside page has 2x4" area signed in lead pencil "Sincerely Frank Sinatra Buddy Rich" just beneath text "Cocktail Dancing Every Saturday 4PM Til 6PM During Tommy Dorsey's Broadcast". Menu was likely signed before or after this broadcast. Extensive menu includes broiled filet mignon for $2.00 and roast prime rib of beef for $1.30. Covers have bit of wear, most noticeable on back cover which has a few color rubs at top edge of photo. Inside has bit of age toning with a few tan marks here and there but overall Fine with Exc. signature area which has been outlined in red pencil by original owner. Frank Sinatra began his career with trumpeteer Harry James and on January 26, 1940 he made his first public appearance with the Dorsey band. During the first year with the Dorseys, Sinatra released more than 40 songs which puts this menu right in the middle of that achievement. Drummer Buddy Rich first played jazz with a major group in 1937 and in 1938 he was also hired to play in Tommy Dorsey's orchestra where he met and performed with Frank Sinatra. Wonderful vintage item for two great performers early in their careers. Comes with Hake's COA and JSA LOA.