This is a great list, and thanks for making the playlist, Peter2! The concept was thought up by the great Mark Eden Horowitz of the Library of Congress, as you've said above, who wanted to do a concert at the Library of songs Sondheim had written for his 70th birthday.
According to Horowitz, Sondheim was perfectly fine with the idea of (another) concert celebrating his work (what a snooze, more people singing your praises and your music!), but when Horowitz suggested that, instead, they could perform songs he wished he'd written, Sondheim lit up, and would fax Horowitz constantly for an extended period of time as he thought of more songs for the list and revised it. They ended up performing just a fraction of the whole list at the concert (it's long), but printing it all on the program, as well as thank you's and birthday wishes from all of the composers and lyricists listed who were still alive. As another poster pointed out, the wonderful Frank Rich then reprinted this list in the NYT --- he's sometimes erroneously credited with coming up with the idea, but he does deserve credit for making the list more popular! And then Horowitz reprinted the list in his wonderful "Sondheim on Music" book.
(At the concert, they also performed all of "The Frogs," or what there was of it pre-Broadway... which then led to the Broadway production, as Nathan Lane hosted the concert.)
"I Had Myself a True Love" is my favorite song ever written, and I love the recording that Peter2 has put on this playlist but also urge everybody to listen to Audra McDonald's recording of off "How Glory Goes," as well as the incredible many recordings of the song by Barbara Cook. (The concert and list was inspiration for Barbara Cook's "Mostly Sondheim" concerts, where she performed Sondheim's songs next to those on the list).
One song that didn't make it onto the list, who knows why, but that he loved --- Sondheim wrote a letter to Lynn Ahrens saying that he had to pull his car over crying after hearing her song "Times Like This" from Lucky Stiff and that it was one of the most beautiful songs ever written. It's a lovely song and there's a great Liz Callaway recording on Spotify.
"I feel safe with you, and complete with you / I'm always finding money in the street with you."
-Sheldon Harnick