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With the passing of Jesse Winchester I decided to see just how many of his songs Jimmy Buffett as recorded over the years. Jimmy's love of Jesse's songwriting abilities goes all the way back to the album "Havana DayDreamin" in 1976 and continued through the release of Songs From St. Somewhere in 2013. Jimmy has recorded just six of Jesse's songs on his own albums plus a seventh song for the 2012 Jesse Winchester 2012 tribute album entitled "Quiet About It".

Here is the list of Jesse Winchester songs recorded by Jimmy on his own albums:

Defying Gravity - Havana DayDreamin 1976

Biloxi - Changes in Attitudes, Changes in Latitudes - 1977

L'Air de la Louisiane - Hot Water 1988

Nothin' But a Breeze - Take The Weather With You - 2006

Rhumba Man - Buffet Hotel - 2013

I Wave Bye Bye - Songs From St. Somewhere - 2013

Jimmy also recorded the following song for the 2012 Jesse Winchester tribute album:

Gentleman of Leisure - Quiet About It - 2012 Jesse Winchester Tribute album

Funny, I did the same thing. Probably going to throw them together on a little playlist, will probably add the live version of Mississippi on my Mind as well.

He didn't record them but he's done Brand New Tennessee Waltz and Club Manhattan in concert. Not often, maybe only 2 or 3 times.

Jimmy sang Gentleman of Leisure at the Montessori School Benefit Show at Guild Hall in East Hampton NY on 11/4/2000.
I had a download of it before my hard drive crashed, so I think it must be out on the Concert Trading forum.

According to the BN set list database he has performed Gentleman Leisure live a total of four times:

03-21-2002: Dukes Waikiki Restaurant – Waikiki Beach, HI
05-04-2001: Margaritaville Cafe – New Orleans, LA
11-04-2000: Guild Hall – East Hampton, NY
06-02-2000: Unknown – Charleston, SC

Threw 'em all together in a quick little playlist as follows:

1. Gentleman of Leisure
2. Rhumba Man
3. Defying Gravity
4. Nothin' But a Breeze
5. Biloxi
6. L'Air de La Louisiane (live)
7. I Wave Bye Bye

Was going to add the live version of Mississippi on my Mind from Gulf Shores, but realized while listening that JB doesn't sing on the track at all, so I left it off. But Jesse is fantastic on it.