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Beaches, Bands & Bars

Dedicated to the people and places that make "Life's A Beach" more than just bumper sticker wisdom - whether that beach is at your back door or, like Margaritaville, just in your mind. From beach bars and boat drinks to Parrot Heads and Trop Rockers...

Yankee Jack, Key West Conch-troversial

Sitting up close to hear Yankee Jack in a bar  is like being in the front row at a Gallagher show – eventually, you’re gonna get hit with something. Only, in Jack’s case, it’s not sledgehammered fruit – it’s humor, mostly of the “not politically correct” variety. Tourists, foreigners, gays, fat people, skinny people, women with large breasts – breasts in general. They all get lovingly attended to (or skewered) at a Yankee Jack show. Typical Jack Joke (paraphrased): “They’re outlawing mini skirts on Duval Street. The problem is the testicles hanging below the hemline”. Bad-dum-bum. If you’ve been to Key West, chances are you’ve heard Yankee Jack. He holds court most weekdays at the Bull and Whistle on Duval  and – given the open air layout of the first-floor Bull – the laughter and music is usually heard spilling out into the street.

Key West Conch-troversial, Jack’s latest cd of original material, is a conglomeration of “straight” material with plenty of his over the top musical comedy. The opening track, a tribute to his adopted home town (originally from new England, Jack moved to Key West in 1989) “Cayo Hueso”, mixes the two. One minute he’s singing about sleeping on the beach under the stars, the next he’s admiring a woman with “a great caboose”. “Same Sex Sunday” is not about spending part of the weekend hanging out with your own gender, like the title might imply. Instead, it’s an ode to stuck in a rut marriages (“What we used to do like stars of porn is scheduled now for Sunday morn”). “Jesus Was a Democrat” will probably tweak those on the Right but, then again, Conservative has never been a word associated with Key West. “The Last Mudslide” is a musical shout out to Jack’s main employer that floats a familiar theme  – a Key West visitor that isn’t quite ready to head back home (“I’m strapped in a plane and I wish I were back – drinking Mudslides on the bar at the Bull”).

More of the larger than life Yankee Jack’s humor appears on “If It Flirts, Floats Or Flies, Rent It” (“A woman gives you nookie, but she might wind up to look like Snookie”) and the title track, another tribute to his adopted island home, “Very Conch-troversial” (“The Southernmost point is my new home, I come from a land they call bitch and moan, and half this island’s getting stoned”). But, just when you think you’ve got Jack figured out as a jokester and humorist, he slides comfortably into a soft piano ballad like “The Sea”, or a catchy Trop rock toast to a seaside town, like “Casco Bay”.  

For a taste of Jack’s live show, check out his cd, “The Best Of Yankee Jack Live in Key West”. Just don’t sit too close to the speakers.   http://yankeejack.com/






Yankee Jack's a blast - and that's no bull!
by Dick Conklin

You are doing the Duval Crawl one afternoon when you come to the corner of Duval and Caroline Streets. The open air bar on the corner is filled with a noisy crowd that is laughing at the guy playing the key- board. His songs are absolutely outrageous, so you stop to listen. A few minutes later you are inside, finding yourself taking audience participation to a whole new level. Congratulations - you have just become part of The Yankee Jack Entertainment Experience.

Yankee Jack, a.k.a. Jack Pittorino, sometimes refers to himself as The Biggest Performer in All of Key West. This big guy is big on music and big on comedy, and his shows are pure Key West. He can draw in both tourists and a few stray locals with his off-the-wall lyrics and humor, and everyone is sure to have a good time.

Jack plays guitar and keyboard, and sings an interesting mix of music, from country and folk to 50's and 60's rock and - of course -

some Jimmy Buffett thrown in. Much of his music has a definite local flavor, written in a style he likes to call "Key West Country."

Yankee Jack's songs are known far and wide. While we can't list all of the titles in this "family newspaper," we can mention a few of them. The other night we stopped at Larry Smith's Sunday Showcase at the Pier House, and someone took the mike to sing "Manatee Woman" - a Yankee Jack original. Others include the infamous "There Ain't Enough Whiskey in Tennessee To Drink The Ugly Off of You," "Botox Bimbo," "Are You Deaf or Stupid?" "Beauty is just a Light Switch Away," and a personal favorite, "Boca Raton".

Recently we ran into Jack at a private party, where he played just the right kind of music for the crowd, a "PG-rated" version of his Bull routine. Sales of his six CDs are brisk, since many who catch his gig at the Bull want to take the show home with them. The most recent, "The Best of Yankee Jack, Live," and his video, "Live at the Bull," capture his unique form of Key West music and humor. The CD features his 25 most requested


originals. You couldn't find a better souvenir of the Southernmost City.

The Massachusetts native has been performing professionally since 1964, and has been in Key West for the past sixteen years. These days you can find him at The Bull & Whistle Bar every day except Wednesday from 1 - 5 pm, and at the Geiger Key Marina every Friday between 6 and 9. He also plays the Sugarloaf KOA on a "random basis."

Before becoming a Key West funny man, he worked the country circuit, opening for superstars like Willie Nelson, Loretta Lynn, the Oak Ridge Boys, B.J. Thomas, Tammy Wynette, Mel Tillis, Charlie Daniels, Eddie Rabbit, and Wilson Philips. He says that Willie Nelson and Jimmy Buffett have had the most influence on his music.

While living in New England, Yankee Jack won over 50 state, regional and national country music awards, was a headline performer on over a dozen cruise ships, and starred in his own

cable TV show.

Jack says that music is his only business. "1 have no day job... my Father asks the same question," he says. "I play golf and have a wife, Kate, from Wales who I met on the Internet, hence the song 'Interface' - check it out:' He plans to continue playing the Duval Street music scene, but he wouldn't mind having some of his songs "discovered by some superstar:' As you might imagine, this guy has plenty of stories to tell, both on stage and off. "The most memorable one was about the two Brazilian women. Come into the Bull and I'll gladly tell you all about it," he says.

You can find a cyberspace version of Yankee Jack on his Web site, www.yankeejack.com. or the real version l at 305-292-9832. Now, about those two Brazilian women. . .

Dick "Conch" Conklin is a freelance writer who lives in and writes about the Florida Keys. He can be reached at conch@keysy.com or (305) 743-8243.



Your best source of print and online news from the Florida Keys
Yankee Jack cracks us up! Posted-Friday, October 22, 2004 3:03 PM EDT
Renowned Keys singer releases live album

Yankee Jack fans, who have long been asking for a live compilation of his best loved songs and corny jokes, are finally getting their wish: "The Best of Yankee Jack - Live in Key West."

The 25-track CD was recorded at the Bull and Whistle Bar on Duval Street and mastered by Francois at Mad Dog studios here in Key West. Local artist Letty Nowak painted the cover portrait and the graphics were created at her Lemonade Stand Art Gallery.

Jack writes on a wide variety of subjects and in different musical styles. His songs are funny, sentimental, irreverent, sometimes risque, but always entertaining. A few particularly hilarious tunes include:


'The Best of Yankee Jack - Live in Key West' is available now. The CD has 25 fun-filled tracks from his shows, live, at the Bull.
"There Ain't Enough Whiskey in Tennessee to Drink The Ugly Off Of You," "Botox Bimbo," "Freeboobinit," and "(Bill Clinton's Song) Sex Between The Bushes."

Each song is prefaced by stories and jokes, some of which include audience participation.

This is "Key-zee" music that vacationers and residents alike have been listening to live and then taking home as a token of happy memories. Yankee Jack's uncomplicated writing, coupled with catchy tunes, makes for a CD with something for everyone. Drop by the Bull any day (except Wednesday) from 1 to 5 p.m., or visit his Web page at www.yankee jack.com for details.

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