This came out in 2004 – or at least that’s when I got it. Here’s what I said about it back then (with some minor editing):
Everybody wants to be something they’re not. Comics want to be taken seriously. TV stars want to be singers. And Regis Philbin wants to be Bing Crosby.
So on When You’re Smiling — his first album in 36 years — he cranks down his abrasively chipper persona and blandly croons oldies like Pennies From Heaven and Cheek to Cheek, backed by a slick but uninspired jazz combo. And whether he wants to be, or not, he ends up being something he’s usually not: Boring.
