Eighteen Connick, seventeen Bublé. Two men who built careers on the Great American Songbook, thirty years apart, and a genuinely close contest.
The tale of the tape
Harry Connick Jr. is from New Orleans, the son of a district attorney, and was a serious jazz pianist before he was a singer — he studied with Ellis Marsalis and James Booker, which is roughly the best musical education available anywhere. His breakthrough was the 1989 soundtrack to When Harry Met Sally, and his 1990s big-band records were his own arrangements, played by his own orchestra. He has also acted extensively and led relief efforts in New Orleans after Katrina.
Michael Bublé is from Burnaby, British Columbia, and came up singing standards in clubs before being discovered by David Foster. His skill set is different: he is a superb pure vocalist and one of the great living entertainers, with an instinct for making a two-thousand-seat room feel small. He has sold vastly more records than Connick.
Round by round
Connick leads on musicianship. "It Had to Be You" and "Let's Call the Whole Thing Off" are from the Harry Met Sally sessions and remain definitive. "We Are In Love" and "Recipe For Love" are his own compositions, which matters — he writes in the idiom rather than only performing it. "Stardust" and "I Only Have Eyes For You" show the pianist. "And I Love Her" reworks the Beatles into New Orleans time.
Bublé answers on voice and warmth. "Home" is his own song and the one that made him a genuine star rather than a covers act. "Kissing a Fool" — the George Michael song — is arguably the best thing he has recorded. "Me and Mrs. Jones" takes on Billy Paul, which is brave, and "Georgia on My Mind" takes on Ray Charles, which is braver.
The Naturally 7 collaborations — on "Have I Told You Lately" and "Stardust" — add a vocal group behind him and are among his most interesting arrangements.
Both cover "The Way You Look Tonight" and "The More I See You," which makes the comparison direct. Play them back to back; it is the clearest illustration of the difference between a musician who sings and a singer who employs musicians.
The verdict, and where to go next
Connick wins on depth — the piano playing and the writing give him range Bublé does not attempt. Bublé wins on the voice and on sheer likeability. Reasonable people land either way.
Albums: Connick's We Are in Love (1990) and She (1994), the funk record nobody expected; Bublé's It's Time (2005).
And for the source: Frank Sinatra's Capitol years with Nelson Riddle, Nat King Cole, and Ella Fitzgerald's Songbook series. Both men are working in an enormous shadow, and both know it.

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