Post is kindda triggered by the Buddy Holly thread...more due to proximity of timing. So, I often fall asleep listening to Amazon Music on my Kindle. The other night, I selected "mellow jazz" (sic) playlist. Now typically I prefer instrumental jazz (though not against vocals - I wake up to Nina Simone every morning), but the first song in the playlist was a vocal performance and I was about to skip it, but listened, and soon became transfixed. I was totally unfamiliar with Blossom Dearie, and there are so many aspects of her performance that, on paper, I would go thanks, but no thanks. There is that pixie, cutesy quality to her voice; the type of songs she plays that seem novelty - kitschy; her name...but her vocals simply work on so many levels, and she is quite the pianist. I have been playing a lot of her music of late, trying to see if I tire of it, cause I feel I should for the reasons I mentioned, but nope! I really do not get it, but that is why she is an Artist. (and talk about a left curve here: She falls into the same category as Ice-T for me: I do not like, but appreciate, Rap but Ice-T's Original Gangster was one of the most revelationary experiences I had when I first heard it).

Anyone else know of Ms. Dearie, my current crush?

I have several albums by her, but I am afraid I also fall into the camp who doesn't normally like the qualities you listed as "Thanks, but no thanks" and she doesn't transcend them for me.
But I haven't played anything by her in a while, so I'll throw them on again over the weekend and see how I feel. I know she is talented, and I often appreciate artists more if I give them another chance.
I am currently playing Billie Holiday, and I never get tired of her. Loved her when I first heard her in the 70s, and still do.

My wife's a big fan.

She sang a few "Schoolhouse Rock" songs, which is where I discovered her.

I have been a fan of hers for some time. There are times when you couldn't force me to listen to her, but at others she fits the bill perfectly. As with many other performers, it depends on the mood.
This is a nice comp that has much of her best stuff, including her wonderful version of "Manhattan", which is what got me listening in the first place. Most of her music is readily available on Amazon, and at good prices.

I've long been a fan of Blossom. I find I rather like the little girl type voice sometimes, and it reminds me a lot of Mildred Bailey.

As for the cutesy aspect, remember where she is on the jazz timeline. Her pop-jazz prime comes out of the late '50s, a decade in which Doris Day was a popular singer, and that particular side of the jazz wheel was not interested in going bop or modal or getting too serious like Billie. Popular mainstream, feel-good, jazz was more about Frank Sinatra's 'Songs for Swingin' Lovers' and Take Five and even Lambert, Hendricks & Ross than it was about the deeper and more layered straight-ahead jazz of the day like Coltrane or Monk.

Schoolhouse Rock inspired me to buy CD's by Blossom Dearie, Bob Dorough, Jack Sheldon, and Dave Frishberg, and I've discovered some great music from all of them. The album I have of Blossom features recordings from about 20 years prior to her Schoolhouse Rock work. Her approach is straight ahead and delicate (both her vocals and piano playing). "Mellow Jazz" is a good category for her - if we have to categorize.

Never heard of her.