Anita's ability to sing in fast tempos set her apart from any of her peers in any of the eras in which she contributed memorable performances. This ability made her highly successful with Gene Krupa and his orchestra, and allowed her to seamlessly segue into bebop and beyond as the swing and big band eras died.
She also had long associations with other drummers, notably Don Carter and John Poole. Carter, her first husband, gave her drum lessons. Poole was her favorite drummer and she maintained a professional association with him that spanned over three decades.
Here is a great video of Anita and John Poole (see also the 1958 Newport Jazz Festival clip further on):
I consider her male counterpart to be Mel Torme, who shared her ability to sing in fast tempos, and was a solid drummer in his own right.
There are some excellent biographical sources that balance Anita's Jezebel antics with her musical accomplishments and contributions to jazz:
- John Poole's wife, Elaine, wrote a revealing biography, Jazz, Jail, and Genius: Adventures and stories of singer Anita O’Day and her drummer John Poole
- Anita's own autobiography, High Times, Hard Times, is as open and revealing as Elaine Poole's bio above.
I also highly recommend her bio pic, Anita O'Day - The Life Of A Jazz Singer, which comprehensively details her story without the usual embellishments or convenient lapses of less than flattering material that characterize many biographies. Other sources of information that I found to be balanced and accurate are Lara Pellegrinelli's 2002 article, Anita O’Day: Yesterday & O’Day, an NPR Jazz Profiles transcript produced by Joan Merrill, and a surprisingly complete Wikipedia entry. These two audio transcripts of NPR shows featuring Anita are also worth a listen: Anita O'Day: A Distinctive Voice Stilled and Anita O'Day: Revisiting A Classic Voice.
Personally I am not too fond of her early years (except for her stint with Krupa). I believe she hit her stride as an artist when the bebop movement started gaining attention; indeed, I believe that genre was perfect for her talents and musical gifts and set her well apart from any other vocalist of that era.
I have selected the following videos to show how she evolved throughout her career. The highlight for me is her performance at the 1958 Newport Jazz Festival, which was beautifully captured in Bert Stern's Jazz on a Summer's Day.
With Stan Kenton
At the 1958 Newport Jazz Festival(John Poole on drums)
Because her music spans many albums and genres I am reluctant to make firm recommendations. Here is a list of Anita O'Day Albums, ranked by highest reviewer ratings, that can guide you.
There are videos in addition to the ones I listed above that I do recommend: Jazz Icons: Anita O'Day Live in '63 & '70, Live in Tokyo '63 and Anita O'Day - Live at Ronnie Scott's all capture this great woman in excellent performances. Enjoy the music!