The album features Jobim's grandson Daniel Jobim on piano and vocals, whose parts were recorded in his native Brazil.[3] Other backing vocals are provided by his wife Jessica Molaskey, and daughter Madeleine Pizzarelli.[4]
The tracks include Antonio's Song, a tribute to Jobim by Michael Franks[5] whom Pizzarelli also cited as a hero of his.[6] Also included are two new tracks written by Pizzarelli and Molaskey.
Matt Collar of AllMusic rated it with the best of John Pizzarelli's albums to date, with 4.5 stars. He commented "Sinatra & Jobim at 50 works as both an homage to two of Pizzarelli's biggest influences and a revealing showcase for his ever deepening musical palette," and that "the album was an unexpected delight for fans."[2]
C. Michael Bailey summarised the album for All About Jazz as a "quiet, breezy affair of lilting Brazilian rhythms and melodies played by a crack team of musicians." He commented "singing and guitar playing are of the level we have come to expect of Pizzarelli, who has matured fully into this role of keeper of the flame for this flavor of jazz music."[8]
Will Friedwald of The Wall Street Journal ended his review saying the album "succeed[ed] at maintaining a tricky balance: staying true to the [original] while, at the same time, creating something new and exciting out of music already considered classic.[9]
Christopher Louden wrote for the JazzTimes that "Pizzarelli revisits the Sinatra-Jobim oeuvre with sublimely honorific results."[10]