Frank Sinatra is rightful known today as an entertainment icon, but many forget that there was a time when he was just another washed up teen idol trying to reinvent himself artistically and revive his career. After his teen idol stardom ended, Sinatra went through a rough period that he described as ‘all Monday’s’ when his personal life was in shambles, his professional prospects non-existent and his financial status in ruin.

To make matters worse, the impresarios at Columbia Records were abusing his talent in an effort to revive his album sales. His pairing with producer Mitch Miller was particularly disastrous. The nadir of this unholy alliance was probably the recording of “Mama Will Bark”, where the greatest voice of the 20th century shared the microphone with a buxom actress named Dagmar (sort of a Rhonda Shear of her day) and some other ‘vocalist’ howling and barking like a dog in the background. Not surprisingly, Sinatra’s recordings with Mitch Miller were not a resounding commercial success and in 1952 he was dropped by Columbia.

His luck was soon to improve, however, as a number of his colleagues including former Tommy Dorsey vocalists June Hutton and Jo Stafford got him in the door at Capitol Records. This began a nine year relationship that produced some of the finest work of Sinatra’s career. Initially, Frank worked with June Hutton’s husband, Axel Stordahl. These sessions produced some decent music including “I’m Walking Behind You” but wouldn’t last long. Frank wanted to go in a different direction, which became a necessity when Stordahl left to take a gig with Eddie Fisher in New York. After a lengthy search for a replacement, Sinatra reluctantly agreed to work with an experienced big band conductor named Nelson Riddle. The Capitol Records executives were excited about the matchup, but Sinatra had to be convinced.

To say that the first Sinatra/Riddle session was a success is an understatement, and “I’ve Got The World On The String” is somewhat of a ’shot heard round the world’ for Sinatra’s career and popular music in general. The Ted Kohler/Harold Arlen song is given new vibrancy with Riddle’s buoyant arrangement and Sinatra’s new found vocal maturity. The song was a modest commercial success at the time, reaching #14 on the single charts, but became a classic. It was also a favorite of Sinatra himself, and he continued to perform the song live, frequently as a show opener, for the rest of his life.

Put into a modern context, Frank Sinatra’s career is even more remarkable. It’s difficult to envision one of today’s popular acts among the adolescent set like the Jonas Brothers being able to even transition into a career where they’re taken serious as an adult artist. Sinatra far exceeded that goal, leaving an imprint on popular music that may never be equaled. His ascendancy to his status as ‘Chairman of the Board’ and one of the most important artists of the 20th Century all began with his union with Nelson Riddle.

Frank Sinatra is often dismissed as a mere ‘pop’ singer and critically diminished relative to his contemporaries. He’s often accused of being formulaic and repetitive and not afforded the proper respect for his vocal talent. While Sinatra certainly knew what worked for him, and what kind of songs and arrangements he liked, the assertion that he didn’t have the vocal ‘chops’ is patently unfair. Perhaps the finest example of his vocal excellence is his work with Brazilian guitarist Antonio Carlos Jobim.

Jobim is considered the founding father of Bossa Nova, and certainly deserves a bulk of the credit for popularizing the genre in North America. His collaboration with Sinatra on a samba tinged album Francis Albert Sinatra and Antonio Carlos Jobim was a critical and commerical success. Sinatra had the highest respect for Jobim as an artist and liked him as a friend. He would try to work out the logistics for the two to record together at several points in his career, but it never came to pass.

“Wave”, written by Jobim and arranged by Eumir Deodato, is perhaps the finest of their collective work. It features some magnificent technical singing by Sinatra, including what are the lowest notes ever recorded by “The Chairman of the Board”. For the rest of his life Sinatra enjoyed listening to ‘Wave just to hear how good he sounds hitting the bass notes.

This song originally intended as the opening track of a second volume of Sinatra/Jobim collaborations, but it was never released as such. The story that has circulated over the years is that the Sinatra/Jobim album put on the back burner so that Reprise could release the concept album “Watertown” instead. As an commercial decision, it’s tough to fathom the rationale if this is the case. “Watertown” sold fewer copies than any other Sinatra release on Reprise. Another story is that Sinatra himself nixed the release because he hated the cover art which featured the ‘King of Swingers’ wearing a windbreaker and standing in front of a Greyhound bus. Hard to blame him for disliking that image if this version of the story is true.

“Wave” finally surfaced on “Sinatra and Company” in 1970. “Wave” also appeared on the Reprise box set and of course of the “Complete Reprise Recordings” suitcase collection.

Will Friedwald, in his definitive book on Sinatra’s music “Sinatra: The Song Is You” described the singer’s work with Jobim as having “flexibility and delicacy, as if they could be blown about by a soft Brazilian breeze”. This sensual and sultry song, in particular, is among the finest vocal work of Sinatra’s amazing career.

Frank Sinatra is often dismissed as a mere ‘pop’ singer and critically diminished relative to his contemporaries. He’s often accused of being formulaic and repetitive and not afforded the proper respect for his vocal talent. While Sinatra certainly knew what worked for him, and what kind of songs and arrangements he liked, the assertion that he didn’t have the vocal ‘chops’ is patently unfair. Perhaps the finest example of his vocal excellence is his work with Brazilian guitarist Antonio Carlos Jobim.

Jobim is often credited with popularizing Bossa Nova music outside of Brazil. He worked with Sinatra on an album of samba tinged standards entitled Francis Albert Sinatra and Antonio Carlos Jobim. The work was a critical and commercial success, and Sinatra would hold Jobim in very high regard for the rest of his life”both as a musician and as a friend. After Jobim entered a semi-retirement in the 1970s and 1980s where he did little collaboration with other artists, Sinatra would often introduce his performances of Jobim songs live by remembering his Brazilian colleague in very fond terms or expressing the hope that the two men could work together in the future.

“Wave”, written by Jobim and arranged by Eumir Deodato, is arguably the best of all of the Sinatra/Jobim collaborations. It features some great singing by Sinatra, including perhaps the lowest notes ever recorded by “The Voice”. Years later, during his periods of ‘retirement’ it is said that Sinatra would listen to “Wave” just to hear how good he sounds hitting the bass notes.

This song originally intended as the opening track of a second volume of Sinatra/Jobim collaborations, but it was never released as such. The story that has circulated over the years is that the Sinatra/Jobim album put on the back burner so that Reprise could release the concept album “Watertown” instead. As an commercial decision, it’s tough to fathom the rationale if this is the case. “Watertown” sold fewer copies than any other Sinatra release on Reprise. Another story is that Sinatra himself nixed the release because he hated the cover art which featured the ‘King of Swingers’ wearing a windbreaker and standing in front of a Greyhound bus. Hard to blame him for disliking that image if this version of the story is true.

“Wave”, along with the majority of the songs intended for the “Sinatra/Jobim” album finally surfaced on “Sinatra and Company” in 1970. The “b” side is some of Sinatra’s ill-fated attempts to cover popular songs of the day (”Close To You”, It’s Not Easy Being Green”, “Leaving On A Jet Plane”). These are recordings that even the most rabid Sinatra fans consider among his most forgettable work, and a stark contrast to the masterful collaboration with Jobim on the album’s “A” side. “Wave” also appeared on the Reprise box set and of course of the “Complete Reprise Recordings” suitcase collection.

Critic Will Friedwald, who may have written more about Sinatra’s body of work than anyone, praised his recordings with Jobim as having a “flexibility and delicacy, as if they could be blown about by a soft Brazilian breeze”. In any case, the Sinatra/Jobim sessions certainly rank among the finest vocal work of Sinatra’s amazing career.