Cavolina reunited with Anita O’Day, when, “In 1999 I found out that she was very ill, so I phoned her manager to ask if I could go over to see her. He said sure come on over and he said by the way the rights (to a film) are available. I sold everything that I had (to obtain the rights). I had just started a little editing company, so I thought I could make a film.  Anita and I became friends and I got close to her. I started studying her and listening to all of her records. I found everything that I could about her and watched all her video tapes so that I could really understand her. Then I read the book (High Times Hard Times) and I (initially) thought that I was going to make it into a feature film, a biopic. Later, when Ian came into the picture in 2003, he said that I should make the documentary, because it would seed the picture. He told me to do the documentary first. I asked Anita if she would want us to do that and she said ya” 

 

As Cavolina became more involved with Anita O’Day and in her later years acted as her manager, McCrudden and Davis’ interest in making a documentary grew. McCrudden says, “Melissa raised some financing pretty quickly. It all began with seeing Anita O’Day singing, and feeling that there was a story there. It was a little rough shod, because in some of her shows she was drunk. I was however, interested in this person who continued to do her art, as though it was her whole life.”

 

The two producer / directors could have spent more time focusing on the more sordid details of Anita O’Day’s life but just as they were not out to glam up who she was, neither were they intent on only exploring her addictions and what at times could amount to destructive behavior. They set out instead to create a balanced, but realistic movie which possesses some stunning archival film footage of the singer’s performances, including one section of the film where four separate clips of her singing, “Let’s Fall In Love,” are presented in a montage.

 

“We couldn’t decide which one (video clip of “Let’s Fall In Love”) to put in, so I said to Ian let’s put them all in. She was giving Dr Billy Taylor a lesson on improvisation, so I thought why not show it all, because she is doing it four different ways.,” says Cavolina.

 

For his part, Cavolina did not want Anita O’Day Life of a Jazz Singer to reflect what he had watched in numerous other jazz documentaries. “I had seen every single jazz documentary on the planet. I cried while watching Louis Armstrong’s and Chet Baker’s was so, so sad. The stories of Billie Holiday and Charlie Parker were also sad. I thought these guys weren’t sad. Not to diss documentary filmmakers, because I think they want to tell a story, and yes if you put their stories on paper, a lot of the things that these people went through is sad, but they were brilliant people, who were able to do one of the most difficult things, which is to improvise music, with instruments that most people can’t even play.”

 

Cavolina remembers, “I asked Anita one day, what jazz is and she said, it is having the ability to improvise, make it up as you go, and to be good at it. She lived her life one hundred percent for music. She was like Vincent Van Gogh, who just painted, painted and painted. She said, ‘I got good, because I just did it, did it and did it.”

 

Both directors made sure that any comments that were made about Anita O’Day’s use of heroin and alcohol abuse came from archival footage of her interviews.

 

“It was fairly well documented in her own book that she struggled with substance abuse and had multiple abortions. The book was a little bit of a tell all.  The decision as to how to handle it was taken from what she would talk about herself. If you notice, in the movie, we do not have anyone else speculating or gossiping about her use of drugs. You see what she says about it, either to an interviewer like Tom Schneider, Dick Cavett or Harry Reasoner.  The thing that I would say about Anita is she didn’t glamorize it or think that it was cool. She is not proud, but on the other hand, I don’t think that she is regretful. The trick was to try and show it the way that she sees it,” says McCrudden.