April 2024 Newsletter

Sloppy Joe's Bar, Key West | April 2024

Sloppy Joe's Bar, Key West | April 2024

Sloppy joe's bar building in key west

May 5, 2024, Sloppy Joe’s Celebrates 87 years on the Corner of Duval and Greene Streets

The victoria restaurant in the 1920's.

The year was 1937; Joe Russell had a heated dispute when then-landlord Isaac Wolkowsky raised the rent on the bar from three dollars a week to a whopping four dollars a week. Joe was so incensed that he decided to move, but a clause in his lease prohibited him from removing any of the furnishings and other accoutrements in the bar. Russell wasn’t going to let a little thing like that stop him. Before long, the determined saloonkeeper solidified his strategy when his lease expired. He soon purchased the nearby vacant Victoria Restaurant building on the corner of Duval and Greene Streets from Juan Farto for $2,500. The majestic building had been built in 1917 and incorporated beautiful Cuban tile floors, whirling ceiling fans, and jalousie doors.

On May 5, 1937, Sloppy Joe’s Bar seemingly disappeared. Wolkowsky, away on a trip, returned to find he was no longer Russell's landlord. With patrons' help, Joe Russell moved down the block and across to the new quarters at 201 Duval Street. The migration was a true Key West spectacle, as customers carried their drinks and the furnishings to the new location. Service resumed quickly with refreshments on the house – the new house – for the rest of the night.

Upon hearing of the move, Hemingway remarked, "Only in Key West."

Sloppy Joe’s Bar’s address may have changed, and its square footage nearly doubled, but its atmosphere remained the same. It boasted the longest bar in town, a walled-off room often used for gambling, and a 119-pound sailfish caught by Hemingway adorning one wall.

If you, like those patrons 87 years ago, are lucky enough to be in Key West on May 5th, join us for an all-day celebration on those same Cuban tile floors.

Sloppy joe’s 1938 photo caption library of congress arthur rothstein
Joe russell behind the main bar
Exterior of sloppy joe's in 1940s fl public library
Interior of sloppy joe's in the 1950s, image from fl public library
Exterior of sloppy joe's bar in the 1970s. Image from fl public library
Interior of sloppy joe's in 1985. Photo by hans dieter klein
Saturdays are 'caturdays' at sloppy joe's bar - noah and teeza

Saturdays are 'Caturdays' at Sloppy Joe's

The Sloppy Joe’s Foundation is proud to announce that its April Caturday partner is The Police Athletic League of Key West.

Key West PAL enriches children's lives by creating positive relationships between law enforcement officers and our community's youth through education, athletics, outreach, and teen leadership programs.

Key West PAL's mission is to provide local youth with focus and direction to help them become responsible citizens within our community. The Key West PAL gym is a volunteer-run center with many Key West Police Officers donating their time to provide quality youth sports such as Kickboxing, Wrestling, and Jiu-Jitsu, activities and educational programs designed to develop their skills, trust, discipline, self-esteem, and respect.

Your donations in April will help provide free memberships to community children and support their much-anticipated summer camp.

For more information or to make a donation, please visit the Sloppy Joe's Foundation. Your generosity is appreciated!

Sloppy Joe's Beer of the Month

Sloppy Joe's Island Ale

In honor of National Beer Day, we wanted to highlight our relationship with Funky Buddha Brewery in Oakland Park, Florida, which uniquely creates our Sloppy Joe's Island Ale; a refreshing Blonde Ale (5% ABV).

You can grab a Sloppy Joe's Island Ale t-shirt online, available in Antique Royal and White. Enter offer code ''save10' for 10% off orders over $50 in the month of April. Excludes gift cards.

Celebrating national beer day, the sloppy joe's island ale
Sloppy joe's bar t-shirts and tank tops

Shop Authentic Sloppy Joe's Bar Key West Clothing and More.

Freshen up your Sloppy Joe’s T-shirt and tank top collection for this spring and summer by visiting our online store.

See what’s in our “on-sale” bin.

10% off online orders of $50 or more. Use code save10. Offer expires 4-30-24. Does not include gift cards.

Laura lea and tripp fabulous

April Band Spotlight

Laura Lea And Tripp Fabulous

Laura lea teaser interview

Click here to see the full interview & a special original song live by Laura Lea!

Musician laura lee on stage
28th annual key west songwriters festival may 1-5, 2024

The 28th Annual Key West Songwriters Festival is May 1-5, 2024

The Key West Songwriters Festival is soon upon us. This annual Festival is slated for May 1- 5, 2024, with over 150 performers and upwards of 60 shows. Sloppy Joe’s is proud to be a host stage with shows on Thursday, May 2nd, and Friday, May 3rd, both at 5:30 pm and back by popular demand. There is a show on Sunday, May 5th, at noon, which happens to mark our 87th year on the corner of Duval and Greene Streets. Saturday, May 4th, Sloppy Joe’s stands tall alongside the festival’s infamous Duval Street Stage, which in the past has featured recording artists Brad Paisley, Sara Evans, Jake Owen, Maren Morris, Love & Theft, Old Dominion, and many more.

Now in its 28th year, The Key West Songwriters Festival has grown into one of the world's largest events of its kind. It is known for its intimate performances in various venues throughout Key West, including bars, restaurants, theaters, and outdoor stages. Attendees can experience live music performances by a diverse array of songwriters and musicians. The festival celebrates the art of songwriting and provides a platform for established and emerging songwriters to showcase their talents in a relaxed and vibrant atmosphere, often with the chance to interact with the songwriters. Sloppy Joe’s has been a host stage for almost two decades, and we look forward to bringing you the faces and stories behind well-known hits and soon-to-be favorite songs.

For the full schedule and more information on the Key West Songwriters Festival, visit https://www.keywestsongwritersfestival.com.

Key west songwriters festival at sloppy joe's.

Sloppy Joe's 43rd Hemingway Look-Alike Contest

July 17-21, 2024

Register Now

2023 papa, gerrit marshall and other papas outside sloppy joe's


5:00 pm

Meet the “Papas” at Sloppy Joe’s. Get to know the contestants and previous winners of “Sloppy Joe’s Hemingway® Look-Alike Contest.


6:00 pm

Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. On stage at Sloppy Joe’s Bar.

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s.

FRIDAY, JULY 19, 2024

1:30 pm

“Papa” Hemingway Look-Alike Fish-Off. Cheer your favorites as the “Papas” compete in this dockside catch-and-release challenge using traditional “Cuban yo-yos” at Conch Republic Seafood Co. docks, 631 Greene Street.

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s.



Photos with “Papas.” Hemingway® Look-Alikes provides a photo opportunity for fans. Happens on Greene Street next to Sloppy Joe’s Bar.

1:00 pm

Running of the Bulls. This wacky event is sponsored by Sloppy Joe’s Bar and features past “Papa” Hemingway® Look-Alike Contest winners dressed in their Pamplona best — and a breed of “bull” found only in Key West. The fun takes place on Greene Street outside Sloppy Joe’s.

HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturday. Those wishing to wear traditional white clothing with a red sash need to be prepared and bring their own clothing (these items are not sold).

6:30 pm

Sloppy Joe’s 43rd Annual Hemingway® Look-Alike Contest – FINAL ROUND to name Papa 2024.

SUNDAY, JULY 21, 2024

9:00 am-1:00 pm

Papa Birthday Bash at Sloppy Joe’s! Bloody Marys with Papas, Photo Opportunities with Papa 2024, and Papa Birthday Cake at noon.

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