Bradley Cooper had the unforgettable role in his FIRST role in Sex and the City in 1999 – 25 years before he became an Oscar favorite

Bradley Cooper is the star of Hollywood and one of the favorites to win an Oscar for his incredible role in Leonard Bernstein's biopic Maestro.

Before his astronomical rise to fame, the now three-time Best Actor Oscar nominee, 49, landed his first acting role in the second season of Sex and the City in 1999.

Bradley played Jake in the episode “They Shoot Singles, Don't They?”, in which he spent a drunken evening with Sarah Jessica Parker's protagonist Carrie Bradshaw.

Carrie has hit rock bottom after an unflattering snap of her hangover and smoking landed on the cover of New York Magazine with the headline “Single and Fabulous?”

After meeting Jake – who Carrie said was everything she was looking for: “single, straight and a smoker” – the two kiss.

Bradley Cooper is the star of Hollywood and one of the favorites to win an Oscar for his incredible role in Leonard Bernstein's biopic Maestro - but his first acting role was a supporting role in Sex and the City in 1999

Bradley Cooper is the star of Hollywood and one of the favorites to win an Oscar for his incredible role in Leonard Bernstein's biopic Maestro – but his first acting role was a supporting role in Sex and the City in 1999

The star was nominated for the Golden Globes on Sunday (pictured)

The star was nominated for the Golden Globes on Sunday (pictured)

But things end when Jake spots Carrie on the magazine cover and shouts, “Is that you?”, causing the writer to jump out of his car.

Carrie met Jake after breaking up with Big for the first time and had all but decided to sleep with the flabby guy to prove she was still fabulous.

He got the role two years before he became famous in the series “Alias” as reporter Will Tiffin alongside Jennifer Garner.

He celebrated his international breakthrough in 2009 in the cult comedy “Hangover” – and celebrated roles in “Silver Linings Playbook”, “American Hustle” and “A Star Is Born”.

Bradley spent six years preparing to play Bernstein by studying the way he conducted orchestras, honing his delivery with dialect coach Tim Monich and working with Academy Award-winning makeup artist Kazu Hiro.

Cooper co-wrote, produced, directed and starred in the 129-minute film, which spans three decades and involves the closeted homosexual's affair with musicologist Tommy Cothran (Gideon Glick).

Best known for his work with the New York Philharmonic and the Broadway musical West Side Story, Leonard won seven Emmy Awards, two Tony Awards, 16 Grammy Awards and the Kennedy Center Honor.

Martin Scorsese and Steven Spielberg produced Maestro

Bradley played Jake in the episode

Bradley played Jake in the episode “They Shoot Singles, Don't They?”, in which he spent a drunken evening with Sarah Jessica Parker's protagonist Carrie Bradshaw

After meeting Jake - who Carrie said was everything she was looking for:

After meeting Jake – who Carrie said was everything she was looking for: “single, straight and a smoker” – the two kiss

Bradley spent six years preparing to play Bernstein by studying the way he conducted orchestras, refining his speech with dialect coach Tim Monich, and working with Academy Award-winning makeup artist Kazu Hiro (starring in the film with Carey Mulligan shown).

Bradley spent six years preparing to play Bernstein by studying the way he conducted orchestras, refining his speech with dialect coach Tim Monich, and working with Academy Award-winning makeup artist Kazu Hiro (starring in the film with Carey Mulligan shown).

The star was nominated for a Best Actor Oscar in 2019 for A Star Is Born (pictured with Lady Gaga).

The star was nominated for a Best Actor Oscar in 2019 for A Star Is Born (pictured with Lady Gaga).

He celebrated his international breakthrough in 2009 with the cult comedy “Hangover”.

He celebrated his international breakthrough in 2009 with the cult comedy “Hangover”.

Bradley's transformation into the legendary composer Bernstein was no small feat.

The Oscar winner's makeup, which included a prosthetic nose to play the Jewish icon and was recently dubbed “Jewface,” required quite a bit of preparation, according to the film's makeup artist Kazu Hiro.

“The final step – he was covered almost everywhere, the body and the arms – that took over five hours,” Hiro told the audience at the film's screening at the New York Film Festival on Monday EW.

Hiro also revealed that Cooper, who is directing the film, extended the call times so he could direct the production in full Bernstein gear while staying in character.

“In the final stages, our call was 1 a.m. the whole time and also he wanted the makeup to be done before the crew called so he could act as Lenny and set up filming and everything.”

“That also meant our call time was two hours earlier than normal, so that was pretty difficult.”