1. The Giant Sexy Jessica Rabbit At Pleasure Island
First opened in 1989, Pleasure Island was an area of Downtown Disney with stores, restaurants, bars, nightclubs, and entertainment were geared toward adults. It was partially closed down in 2008. In 2010, Disney started converting the area to Hyperion Wharf, but that didn't quite happen The area's been in a sort of limbo since then.
2. A Rampaging King Kong
On the Universal side of things, Kongfrontation is generally considered the park's most significant ride closing. Based on the movie King Kong, riders were evacuated from Manhattan in an open-air tram while watching the overgrown gorilla make a mess of things. The ride opened in 1990 and closed in 2002, and was replaced by Revenge of the Mummy.
3. Customers Getting Yelled At For Walking In Through The Wrong Restaurant Door
Ronnie's Restaurant, a Jewish-style delicatessen, was famous for its rigidly enforced policies, abusive waitresses, and mouthwatering hot pastrami sandwiches. After almost 40 years of simultaneously pissing off and delighting everyone in Orlando, this institution closed down in 1995.
4. The Haunted House On Church Street
From 1991 to 1999, downtown was home to Terror on Church Street, a high-quality haunted house experience beloved by locals and tourists alike. It was a popular attraction back at the end of the strip's last real heyday.
5. Hundreds Of Thousands Of People Crammed Downtown For Light Up Orlando
Light Up Orlando was an annual street festival with lots of music, food, and alcohol that ran for 12 years. It was intended to draw visitors downtown, and at its peak, the one-day event drew up to 200,000 people. Its last hurrah was in 1994.
6. A Talking Robot Trashcan Roaming The Magic Kingdom
Push the Talking Trash Can may have been one of the less cuddly or regal characters found at Disney World, but he was somehow so endearing anyway. There was even a local campaign to elect him Mayor of Tomorrowland. Recently though, after almost 20 years, he was retired from this Disney location.
7. A Ride In The DeLorean Time Machine
The first Back to the Future: The Ride opened at Universal Studios in Orlando in 1991, following suit in the Hollywood location in 1993 and the Japan location in 2001. While popular for a long time, Orlando's ride was closed down in 2007 after a three-month stretch operating at around half capacity. It's since been replaced by The Simpsons Ride.
8. The Original Inspiration For Red Lobster
Gary's Duck Inn was an Orlando landmark and Central Florida dining institution for 49 years. In the 1970s and ’80s, it was serving about 25,000 pounds of shrimp every year. Alas, it closed its doors in 1994. The restaurant was purchased in 1963 by Bill Darden of locally based Darden Restaurants and founder of Red Lobster.
9. Sports And Songs At The Amway Arena
This arena was home to the Orlando Magic, Solar Bears, and Predators, as well as the site of countless concerts and other large-scale cultural and entertainment events. It's been replaced by the shinier Amway Center, and the predecessor was imploded on March 25, 2012.
10. A Festival Celebrating Wee Citrus
Oranges and Key limes may hog most of the attention in Florida, but if you were around Orlando more than 20 years ago, you might have attended the city's Kumquat Festival. It featured a spoof on the pageantry typically seen in such events known as the Queen Kumquat Sashay. If you're jonesin' for a kumquat festival today, you'll have to make a trip out to Dade City.
11. That Giant Creepy Winking Wizard At The Mystery Fun House
The wizard awaited above the entrance to the Mystery Fun House. From 1976 to 2001, this attraction was located near International Drive. It had 15 funhouse “chambers,” a cool magic shop, laser tag, mini golf, and other good stuff.
12. Orlando’s Red Hot Mama
Red Hot Mama Ruth Crews worked at Rosie O'Grady's Good Time Jazz Emporium. When it opened in 1974, the nightclub quickly became a go-to spot in Orlando and spurred life on Church Street. After a successful run of more than 20 years, the establishment began losing money and closed in 2001.
13. Food And Fun At Lee's Lakeside
In 2005, Lake Eola lost Lee's Lakeside, a treasured restaurant that had been serving locals and helping them celebrate special occasions since 1980. The restaurant had gone downhill after founding owner Lee Rose passed away about three years before it closed, but Orlandoans who had the pleasure of dining there during its 20-plus great years still remember it fondly.
14. Spring Training At Tinker Field
Florida's an integral part of spring training for MLB teams, and Orlando used to be a part of that. Starting back in the 1930s, Orlando's historic Tinker Field was used by the Brooklyn Dodgers, the Cincinnati Reds, the Minnesota Twins, and the Washington Senators for spring training. Today, Tinker Field's fate is uncertain, having recently narrowly avoided demolition.
15. Vaudeville And Flicks At The Beacham
Sure, you can go to The Beacham in downtown Orlando today. And you even can catch some great local and nationally touring musical acts. But the original Beacham Theater opened in 1921 for vaudeville shows and movies, and in 1963 it converted entirely to a movie theater. It closed in 1975 and the historic venue went through plenty of incarnations over the years.
16. Hoards Of Yellow Plastic Ponchos
The theme parks all offer flimsy plastic ponchos for the tourists who didn't realize it pours every day for a few hours in the summer. Disney World used to have these bright yellow ones with Mickey on them, and they were a common sight. In 2003, though, Disney retired the yellow ponchos and switched to clear ones. It’s unclear why.
17. Needing A Bigger Boat
Jaws, the ride at Universal Studios Orlando, opened in 1990. From the start, it was plagued by bugs and breakdowns, and it had to be pretty much entirely rebuilt. It reopened successfully in 1993. It was quite popular over the years, but ultimately closed down in 2012. You can still see a Jaws statue hanging upside-down in the San Francisco area of the park, though.
18. A Black Cat In The Milk District
Spooky's Black Cat Cafe and Milk District Marketplace was the quirkiest place in that quirky Orlando locale known as The Milk District. Funky music, funky art, friendly service, and fantastic, affordable food made it a special place. Unfortunately, it had a short run, though it earned a respectable number of loyal fans in a brief time. They even miss the spooked-out mural that adorned the building's exterior.
19. Florida's Department Store
Orlando residents and people all over Florida loved their state's major department store, Burdines. The company began in 1896 and spread all over the state through the mid to late twentieth century. It was bought by Federated Department Stores, Inc. in 1956 and rebranded Burdines-Macy's in 2004. In 2005, the Burdines part of the name was dropped for good, and now there's just Macy's.
20. A Slime Geyser
In 1990, Nickelodeon Studios opened in Orlando for television filming and as an attraction. Nickelodeon gradually moved most of its production to California and New York, though, and activity and employees at the Orlando site dwindled. The location closed down in 2005. If you want Nick in Orlando now, there's the Nickelodeon Suites Resort.
21. Pad Thai At Tasty Thai
Tasty Thai was one of the first Thai restaurants in Orlando, operating for 20 years. Located on Curry Ford Rd., it was displaced from the city's Mills50 District hub of Asian cuisine, but its consistently great food easily earned it a spot in the hearts and bellies of locals. Alas, the restaurant closed its doors in early 2014.
22. An 18-Story Pink Birthday Cake With 20-Foot-Tall Candles
In 1996, Cinderella's Castle was converted into a giant birthday cake to celebrate Magic Kingdom's 25th anniversary. The undertaking required 400 gallons of pink paint. The castle was left that way until 1998—well past the 25th anniversary—presumably because the planning, labor, and expense made it seem a little silly to undo it all right away.
23. A Ceremonious Duck March
Every day at 11 a.m, a procession of ducks waddled to the fountain in the lobby of the Peabody Hotel in Orlando and then waddled back to their room at 5 p.m. The hotel, opened in 1986 as the second location following Memphis, was bought by the Hyatt Hotel Corporation in 2013. It's now a Hyatt-Regency, and sadly, they didn't keep the marching mallards.
24. A “Full-Course Golden Fried Chicken Dinner”
That was the famous offering from the Hotel Fort Gatlin, a mid-1920s era hotel that used to be on Orange Ave. It was also known for its high-quality meats and fresh local produce. In 1965, the building was purchased and demolished by the Orlando Sentinel, which is still located on the site today.
25. Wrestling And Bob Dylan At The Orlando Sports Stadium
This venue, commonly referred to as the Eddie Graham Sports Complex, hosted lots of professional wrestling and boxing matches, back when wrestling was real. There were also big-time concerts, like Led Zeppelin, Bob Dylan's Rolling Thunder Review, and Elvis Presley just six months before he died. It opened in 1967 and was demolished in 1995. 
