This came out in 1999 – or at least that’s when I got it. Here’s what I said about it back then (with some minor editing):
The Talented Mr. Ripley’s star Matt Damon displays a new talent of his own — singing! — on the soundtrack to his new psychological thriller.
And not just any song, either; he tackles the classic ballad My Funny Valentine, crooning it soft and low in an androgynous, Chet Bakerish whisper while the Guy Barker quintet quietly swings along. How does he do? Well, let’s just say he shouldn’t quit his day job. But if he isn’t exactly Chet — and after all, who is? — there are some legitimate jazz classics here from the likes of Miles (Nature Boy), Bird (Ko-Ko) and Dizzy (The Champ). Not to mention Gabriel Yared’s original score of eerie, haunting melodies and stabbing, Bernard Hermann accents. A talented lot, in all.