5 Best documentaries on classic crooners

Even though the term may sound unfamiliar to some, it refers to male singers of jazz standards, characterised by a sentimental singing style and their playful relationship with the microphone, always an essential part of their live performances in concert halls, casinos and nightclubs.  

Perhaps you already know many of these artists. We are talking about the likes of Frank Sinatra, Perry Como, Andy Williams, Dean Martin and Bobby Darin, to mention a few. Their popularity reached its peak in the 1960s but many contemporary singers, Michael Bublé and Chris Isaak, for example, are still being inspired by them and incorporated some of their features in their music. 

The biographies and private diaries of crooners are rich in intense love stories, legendary anecdotes, front page scandals, moments of crisis and, obviously,  love for music. These five documentaries masterfully show their troubled human and artistic journeys and offer the viewers a number of unique insights into these extraordinary performers of the 20th century. 

Jon Brewer’s 2014 documentary Nat King Cole: Afraid of the Dark is a candid account of the tremulous life of the Montgomery-born singer and jazz pianist, best known for evergreen hits such as “Smile”, “L-O-V-E”, “Unforgettable” and “When I Fall in Love” as well as for being the only black TV star in Hollywood at a time marked by discrimination and racism.  

Brewer tells the story of the musician through his private journals, mementos, archive footage and a number of interviews to his family members and other stars of the time, such as Tony Bennett, Johnny Mathis, George Benson and Harry Bellafonte. The film represents a comprehensive portrait of a bright mind, a talented performer and a man who played a pioneering role as a Black artist trying to emerge in America’s prejudiced showbiz. 

Alex Gibney’s portrait of Ol’ Blue Eyes is a four-hour long documentary, split in two parts. While the length of Sinatra: All or Nothing At All does not sound promising at all, the subject is so interesting and multi-faceted to justify its run. Time will literally fly by!  

The legendary career of Swoonatra is narrated through the 11 songs played during his 1971 concert in Los Angeles, when he announced his “retirement” for the first time. Here, the singer’s existence is told with no sugarcoating, and his flaws are a core element of his incredible biography. Gibney does not spare the treatment of controversial or delicate themes; the humble origins in Hoboken, the singer’s ties with the mob, his relationship with Mia Farrow and the connections with the Kennedys, among others. 

The director of this film is the singer’s nephew, Chris. While the biased position of the documentarian may have easily favoured the making of a hagiography, interestingly, Chris has been tirelessly working on it for over 35 years, gathering interviews, archival footage and family stories revealing a much deeper and realistic profile of the crooner.  

While this feel-good story is far from being precisely structured, it still manages to keep the viewers hooked thanks to the great amount of exclusive insights into the life of the singer. 

Wolf Koenig and Roman Kroitor’s 1962 film takes its name from Paul Anka’s popular hit. Lonely Boy is not a just a glimpse at the Canadian singer’s early career, but also opens a wider reflection on his transformation process to a world pop idol.  

In just 27 minutes, the two directors are able to provide an intimate—and very fun to watch—account of Paul Anka’s stage life, in line with the spirit of cinéma vérité. The hand-held shots and close-ups seem to treat Anka as a piece of merchandise and depict fans, backers and managers in a grotesque manner.  

Towards the end, Anka sings “Put Your Hand On My Shoulder” in a crowded venue. The scene has an elegant (and surreal) touch; at some point, the ecstatic screams of the fans fade away, while Anka performs his song but, I swear, you will still be able to hear them! 

Finally, a small jewel. Marc di Domenico’s Aznavour by Charles is a charming video essay about the life and career of the French-Armenian entertainer. Apparently, Aznavour himself had been working on this film before his recent death in 2018, and had the chance to preview the first rushes.  

What makes this documentary so magic and poetic (besides the beautifully edited archive footage, shot by le petit Charles himself) is the voice-over commentary, played by actor Roman Duris and heavily based on the singer’s own letters, diaries and thoughts. The viewers will be fully immersed in a time capsule, accompanied by great songs in French, Russian, Italian, English and Armenian (Aznavour was a true polyglot!) and fascinating memories from long-gone decades. 

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