‘Illegally Yours’ Turns 35: Florida, Filming, and Feeling Like the ‘80s

5” x 3.5” color This photo shows visitors on the drawbridge that leads to the front entrance to the Castillo de San Marcos in downtown St. Augustine, Florida. The smaller fortification at the other end of the drawbridge is called the ravelin. The fort tower in the foreground is the San Pedro bastion. The tower at the far end is the San Augustin bastion. The movie ‘Illegally Yours’ was filmed at and near the fort from January to April 1987. The following was noted on the back of the photo: ‘Illegally Yours’.

By: Presleigh Johnson

Public History is everywhere. Whether it’s signs all over St. Augustine, reenactments, or surf culture exhibits, the Oldest City is a treasure trove of history. Being a Flagler College student is one of the best ways to learn about the St. Augustine community.

We all think we know the 1980s: big hair, shoulder pads, Back to the Future, Michael Jackson, The Golden Girls, John Hughes, Ronald Reagan, and “Purple Rain.” 

It’s an era that was fun, funky, and now fused with nostalgia. Some ‘80s fans might ask, “How do we get back to that time?” One answer is to look back at the past through popular culture, especially film. 

Films are time capsules and when you watch them, you’ve uncorked the fashion, culture, and language of a disappearing time. The best way to go back to 1980s St. Augustine is through a little-known film called Illegally Yours (1988). 

Thirty-five years ago, Illegally Yours arrived in theaters. Despite Rob Lowe starring in the film and Peter Bogdanovich directing it, Illegally Yours failed to garner much media attention and did not make it into the canon of ‘80s comedies. For St. Augustinians, however, the film visually transported their hometown to audiences across America.

This photo shows a movie production crew on Cordova Street in downtown St. Augustine. The movie was ‘Illegally Yours’ and it was filmed from January to April 1987. Flagler College is in the background.

(Photo Courtesy of St. Augustine Historical Society)

Before Illegally Yours, St. Augustine was no stranger to the film industry. During the 1910s-1920s, St. Augustine hosted filmmakers and celebrities. To mention a few locations, the Castillo de San Marcos (then called Fort Marion) and the Hotel Ponce de Leon were fitting backdrops for telling stories of historical romances and faraway lands.

Several decades later, St. Augustine again became a popular filming location when Illegally Yours turned different parts of the city into a film set. While today the film might not be remembered much outside of St. Augustine, Illegally Yours gives us insight into 1980s culture, comedy, and filming on location.

St. Augustinians still have memories of when movie stars came to town for Illegally Yours. In true Florida fashion, the cast and crew were served alligator-themed cupcakes. Downtown streets were shut down for filming and some locals remember the excitement of celebrities being seen around St. Augustine. 

(Photo Courtesy of St. Augustine Historical Society)

Filmed in 1987, Illegally Yours’s somewhat convoluted plot revolves around Richard Dice (Rob Lowe), recently back in his hometown, who must serve on a jury for an attempted murder case. The plot thickens when the defendant turns out to be his childhood crush. Enwrapped in a murder mystery, Richard and a group of eclectic characters race around the city hoping to prove Molly Gilbert’s (Colleen Camp) innocence.

This photo shows the actress, Colleen Camp, during the filming production of the movie ‘Illegally Yours’ in St. Augustine, Florida.

(Photo Courtesy of St. Augustine Historical Society)

Some of the film’s most memorable moments involve Lowe’s character wearing a pink bathrobe and later falling off the wall of the Castillo. For me, though, the best part of the film is feeling like I’m back in 1980s St. Augustine.

With its sunny beaches and downtown charm, St. Augustine becomes a central character in the film. Illegally Yours showcases local streets; city landmarks are visible backdrops, including the Villa Zorayda, Bridge of Lions, and more.

The Fountain of Youth, for example, did not change much for the film, but other locations were transformed to fit the story. Richard Dice and Molly Gilbert find themselves in search of a disguise, so they enter the Fountain of Youth and come out wearing 1980s tourist gear, complete with Alligator Farm and Ripley’s Believe It or Not hats. Although the film did not accurately portray all parts of the city, some local businesses and historic sites made cameos.

This photo shows the actors Rob Lowe and Colleen Camp during the filming production of the movie ‘Illegally Yours’ in St. Augustine, Florida. The following was noted on the back of the photo: Rob Lowe. Colleen Camp.

(Photo Courtesy of St. Augustine Historical Society)

“Keeler’s Fort,”—really the Castillo—is the film’s key fictionalized setting. This Spanish fort, because of the plot, is covered in Greek statues, Christmas decorations, and peppered with pagodas. Most notably, the Castillo has a historically inaccurate moat wrapped around it (which Richard Dice falls into).

View of Castillo de San Marcos drawbridge and ravelin (Photo Courtesy of St. Augustine Historical Society)

Locals might be able to spot some location inconsistencies. The current Casa Monica Hotel appears as part of the film’s courthouse exterior, while the courtyard of the Lightner Museum (across the street) doubles as part of the courthouse interior. Just outside the Lightner Museum, Richard Dice naps underneath the Pedro Menendez statue near nutcracker decorations.

10” x 8” copyprint This photo shows the actor, Rob Lowe, in an action scene during the filming of the movie ‘Illegally Yours’ in St. Augustine from January to April 1987.

(Photo Courtesy of St. Augustine Historical Society)

It’s entertaining to see how the film visually transformed such well-known sites and how some locations, especially the streets, stayed the same. Whether it’s Flagler College or the Old Jail, Public History sites pervade the film and provide it with a quirky backdrop. Perhaps that’s why Illegally Yours has been remembered by local Public History leaders as a primary source for re-visualizing St. Augustine.

To Magen Altice, Executive Director of the St. Augustine Historical Society, “The movie was largely seen as a flop. However, when viewed from a historian’s perspective, Illegally Yours is an absolute gem. It offers two hours of jam-packed scenery of St. Augustine as it looked in the mid-1980’s—structures, streetscapes, beaches, vehicles, even the people—all captured beautifully for posterity.”

This photo shows a person wearing a sweatshirt with the wording “Who’s Rob Lowe”. This was during the movie ‘Illegally Yours’ that was filmed in St. Augustine from January to April 1987.

(Photo Courtesy of St. Augustine Historical Society)

The Historical Society hosted a showing of the film and Altice remembers, “When we invited the community for a special viewing of the film at the St. Augustine Amphitheatre in 2018, the result was an extremely fun, 80’s themed evening which brought on a sense of community nostalgia.”

Illegally Yours captured a piece of local history while also building collective community memories. From the silent film era to the 1980s, St. Augustine remains a backdrop for storytelling, perhaps because the Oldest City has already been the site of so much history itself. Small-towns, like St. Augustine, even have their way of inspiring Hollywood’s imagination.

Next time you watch Illegally Yours, see how many St. Augustine sites you can identify.

Click here to search the St. Augustine Historical Society’s database for more Illegally Yours behind the scenes photographs.

Watch the Illegally Yours trailer here.

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