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Rosie O'Grady's Inc company history timeline

1914

The current bridge was built from the 1914 plans by the Walt Disney Company.

1918

In 1918, the former showboat was unmoored and transformed into a summer houseboat for steaming down the tree-lined waterways of Central Florida.

PORTOBELLO YACHT CLUB Pleasure Family Home 1918 Island Founder Merriweather Pleasure built this home for his family who lived on their beloved island for 20 years.

1922

LILLY PLAZA 1922 Originally a turnaround for the limousines of guests visiting the Pleasure family houseboat.

1924

Chandlery and Tool Crib 1924 One of the many support facilities for the cornerstone of Island founder Merriweather Pleasure’s commercial empire, Pleasure Canvas and Sailmakers, Ltd.

1927

On July 3, 1927, a stray spark from Pleasure’s pipe set off an explosion that was heard in Tampa, 82 miles away.

The History Center is located in the restored 1927 courthouse at Magnolia Avenue and Central Boulevard in the heart of downtown Orlando.

1931

After the assembly of the last sail on June 4, 1931, perfectionist Merriweather Pleasure insisted that the factory be preserved intact.

1934

In 1934, the shop was responsible for stuffing the head of a rare Mongolian Yakoose for the Adventurers Club.

1938

Hoping to discover and patent a cheap, clean, abundant, renewable source of power, Pleasure had the building refitted in 1938 as a laboratory for testing “thermomagnetics”—a process designed to harness the earth’s magnetic force.

1940

1, 1940—with Pleasure himself at the controls.

1944

When Hurricane Charlotte damaged the building in 1944, only three years after his patron’s demise, the graphic artist was too dispirited to rebuild.

1954

Doodles, closed the shop in 1954 to join the Air Force as a test pilot for the only customized X-1 ever built.

1955

Their mismanagement led to bankruptcy in 1955; Hurricane Connie hit that same year, and Pleasure Island was abandoned.

1963

He had traveled alone and, like so many other immigrants before and after him, carried little more than his ambitions to make something of himself in New York. It was 1963 and Austin Delaney was in his early 20s, the son of farmers from County Mayo in western Ireland.

1973

New York’s Legendary Steak & Seafood Restaurant was Established 1973, it is centrally located near Times Square, Rockefeller Center, the Jacob Javits Convention Center, Central Park and a short distance from several major museums and renowned hotels.

1974

Oke performed at that opening show in 1974, and he'll perform at Rosie's last show Saturday. "Millions of people have come through those doors," he said recently in the dark hush between shows under Rosie's high, pressed-tin ceiling. "It's sad to see a legend close."

Make no mistake, Orlando had nightclubs in the summer of 1974.

1975

In those early days, "you could practically see tumbleweeds rolling down the empty streets." It was "like Tombstone territory," agrees Spatz Donovan, who walked into Rosie's in 1975 and stayed to become a headliner there for 14 years.

1987

But when the building was reopened in 1987, the automaton was alive and thriving.

1989

As she often said, “If you don’t have something nice to say, come sit next to me!” Restored in 1989 as a joint effort of the Walt Disney Company and the Levy Restaurants.

1991

"Oh, to be at Rosie O'Grady's," read the 1991 Sentinel headline for a soldier's letter, sent back home from the Gulf War.

2000

With deep roots in Orange County, the History Center opened in 2000 and is operated by Orange County and the nonprofit Historical Society of Central Florida, Inc.

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