When you put Oscar-winning screenwriter Aaron Sorkin and the White House together in your head, most of the time you think about The West Wing, the now-iconic TV series he shepherded through its first four seasons at NBC. Before he was chronicling the triumphs and tragedies of the Bartlet administration, though, Sorkin was following a different fictional Commander In Chief: The American President’s Andrew Shepherd (Michael Douglas) and his budding romance with lobbyist Sydney Ellen Wade (Annette Bening).

The film doesn’t have the same devoted following as The West Wing, but it gave birth to many of Sorkin’s presidential hallmarks, and has its own fascinating history. So, 20 years later, we’re taking a new look at some of its most interesting elements.

1. IT BEGAN AS A ROBERT REDFORD VEHICLE.

Though the film ultimately starred Michael Douglas, it started as a vehicle for another of Hollywood’s great leading men: Robert Redford. So, what happened? Well, Redford was reportedly more interested in the film’s love story, while director Rob Reiner was leaning more toward the political subplots. So the two parted ways, and the part of President Shepherd ultimately landed with Douglas.

2. ANNETTE BENING WAS NOT THE FIRST CHOICE FOR THE LOVE INTEREST.

Just as the film began as a project that would star Robert Redford, so too did it originally feature other leading ladies. Redford himself had hoped to land Emma Thompson for the role of lobbyist-turned-President’s girlfriend Sydney Ellen Wade. Susan Sarandon and Michelle Pfeiffer were also considered for the meaty role, and by the time Douglas came onboard Jessica Lange was also up for the part. Ultimately, Bening won it.

3. THE FILM’S PRODUCTION COMPANY OWES ITS NAME TO STEPHEN KING.

Director Rob Reiner also produced the film under his Castle Rock Entertainment banner, founded in the late 1980s and named after the fictional Maine town of Castle Rock, a Stephen King creation also featured in Reiner’s film Stand By Me. Reiner describes that movie as “the film that meant the most” in his career at the time. Sorkin and Reiner collaborated on three Castle Rock films (including A Few Good Men and Malice). The American President was the last of these.

4. THE FIRST DRAFT OF THE SCRIPT WAS INCREDIBLY LONG.

To write The American President, Sorkin shut himself into the Four Seasons hotel in Los Angeles, ultimately cranking out a 385-page script, far longer than the actual shooting script. Sorkin ultimately trimmed down the movie, but the consequences were about more than overwriting: Sorkin became a cocaine addict during his long hours crafting the screenplay. “I was the kind of addict who was functional,” Sorkin told the Los Angeles Times. “I was actually writing good material. But I didn't see people or talk to people. I'd fax my pages over to Rob at 7 a.m. and after we'd talked about it, I'd close the curtains and start writing again.”

5. THE WRITING PROCESS INSPIRED NOT ONE, BUT TWO TV SHOWS.

Sorkin’s long hours writing the script at the Four Seasons ended up producing more than The American President. He took writing breaks at night and spent time watching ESPN’s SportsCenter, which ultimately inspired his first TV series, Sports Night. On top of that, his long hours researching and writing about the White House staff (including scenes in that 385-page script that couldn’t possibly make the movie) inspired The West Wing, which won four consecutive Emmy Awards for Outstanding Drama Series.

6. MICHAEL J. FOX BASED HIS CHARACTER ON A REAL WHITE HOUSE STAFFER.

Lewis Rothschild, Michael J. Fox’s energetic policy advisor who pressured the President on everything from speeches to crucial legislation, was reportedly based on former Clinton advisor and current TV host George Stephanopoulos, as was The West Wing’s Sam Seaborn, Rob Lowe’s character. When asked later which character he most identified with, Stephanopoulos chose The West Wing’s Joshua Lyman, as portrayed by Bradley Whitford.

7. THE OVAL OFFICE SET APPEARS IN MULTIPLE FILMS.

Castle Rock Entertainment constructed an Oval Office set, as well as additional offices, for The American President. Because sets like that come at a premium, they have since been seen in other films, including Nixon (1995) and Independence Day (1996).

8. IT ESTABLISHED SEVERAL OF THE WEST WING’S HALLMARKS.

Because The West Wing grew out of some of Sorkin’s The American President ideas, it’s not surprising to see some of the film’s hallmarks ultimately be repeated during the series. For example, both President Shepherd and President Bartlet have a Secret Service Agent named “Coop.” Plus, both presidents question “the virtue of a proportional response” (The West Wing does this in its earliest episodes).

9. AARON SORKIN MAKES A CAMEO.

Sorkin, whose show business career began in acting, appears as “Aide in Bar” in the film.

10. THERE’S A FRANK CAPRA CONNECTION.

In the film, Sydney makes reference to great American director Frank Capra (It’s a Wonderful Life) when visiting the White House. She wasn’t alone in drawing that comparison. Capra’s grandson, Frank Capra III, served as first assistant director on the film.  

11. MANY CAST MEMBERS ULTIMATELY ENDED UP ON THE WEST WING.

The American President wasn’t just a template for The West Wing in terms of theme; it also featured a number of actors who would ultimately play key roles in the series. Martin Sheen, The American President’s A.J. MacInerney, went on to play the President himself, Josiah Bartlet, on The West Wing. Anna Deavere Smith eventually played The West Wing’s National Security Advisor Nancy McNally while Joshua Malina went on to play Communications Director-turned-Congressman Will Bailey. The list goes on.

12. THE REAL WHITE HOUSE PHONE NUMBER IS USED.

When President Shepherd calls Sydney Wade, he provides a phone number to call him back, to prove that he is who he says he is. That number is the actual number for the White House switchboard, and is used again by Sorkin in a season two episode of The West Wing.