History of the Oscars at the Hollywood Roosevelt Hotel, if walls could talk

HOLLYWOOD, California — The Dolby Theatre, the longtime home of the Oscars, is where film is celebrated. But that wasn’t always the case.

Joelle Garguilo: Where are we right now?

Juan Pineda, The Hollywood Roosevelt: We are in the Blossom Ballroom. This ballroom witnessed the very first Academy Awards in 1929.

Let me paint the scene.

The date: May 16, 1929, inside the historic Hollywood Roosevelt Hotel.

Pineda: The stage was set up over here in the back. We had 270 people that night. It cost you $5 to eat here, which is equivalent now to $90. It was 15 minutes long, to hand out 12 statuettes. It was the only Oscars not on television or on radio.

Garguilo: Who was in this room?

Pineda: You had, of course, the mastermind of the Chinese Theatre and the Egyptian Theatre. You had Douglas Fairbanks, who emceed that night. You had everybody who was anybody.

The first film to win Best Picture was “Wings,” and a special acting honor was awarded to:

Pineda: Charlie Chaplin that evening.

And the celebrity history doesn’t end there.

Garguilo: Let’s take a walk.

Pineda: We’re going to take you up to the Tropicana Pool. This statue was gifted to the hotel because Charlie was such a big part of Hollywood and Hollywood history. So he sits here and greets all our guests as they head to the Tropicana Pool.

Garguilo: Hi, Charlie. Who may have enjoyed a dip in that pool?

Pineda: Well, probably the most famous hotel guest we’ve had – obviously Norma Jeane, who later becomes the great Marilyn Monroe.

Garguilo: She lived here?

Pineda: Norma Jeane comes to live here in 1950. She becomes Marilyn here at the Hollywood Roosevelt.

Garguilo: Through these glass doors is the Marilyn Monroe Suite.

Pineda: Room 229. This is where she lived.

Garguilo: She lived here?

Pineda: From 1950 to 1952, on and off. It was a very special place for her because this is where she gets her big start. She takes her very first photo shoot at the end of this pool. There was a diving board there – there’s a great picture of her. Her career kind of takes off.

Garguilo: Marilyn Monroe may have stood right here.

That’s not all. The hotel served as a set for both television and movies.

Two episodes of “I Love Lucy” were filmed here.

You may recognize Room 208 as the spot where Leonardo DiCaprio and Tom Hanks meet in “Catch Me If You Can.”

And then there’s this:

Pineda: Welcome to 1200, the Gable and Lombard Suite.

Garguilo: You have their pictures right here.

Pineda: This was also home to “A Star Is Born,” Lady Gaga and Bradley Cooper.

Garguilo: One of my favorite movies of all time.

Pineda: As you’re walking in, there’s a great shot of Bradley Cooper passing out on this couch here.

Garguilo: Whoa.

Pineda: And then they spend their first night in that beautiful room. This is the bathroom where she’s talking to the mirror.

Garguilo: This is where Lady Gaga is talking to herself in “A Star Is Born?” In the mirror? Hi, Gaga. Stephanie. Steph.

The bragging rights don’t stop there. This is the only hotel on the Hollywood Walk of Fame.

Pineda: And there is talk out there that for the 100th anniversary, the Roosevelt Hotel may get its very own star.

An incredible honor for a hotel with a deep history that’s still being written.

Garguilo: So on Oscars night, someone, a nominee, will be right here. I’m just going to… oh my gosh.

If only the walls could talk, the stories they could tell.

March 15 is Oscar Sunday! Watch the 2026 Oscars live on ABC and Hulu.

Live red carpet coverage starts at 3:30 p.m. ET/12:30 p.m. PT with “On The Red Carpet at the Oscars.”

Catch all the action on the red carpet live on ABC, or stream on Hulu and OnTheRedCarpet.com.

The 98th Academy Awards, hosted by Conan O’Brien, begins at 7 p.m. ET/4 p.m. PT. and will be followed by “The Bachelorette: Before the First Rose.”