The Oscars are presented for cinematic excellence and the Razzies for being failures. Here we make a list of artists who won both Oscar and Razzie.
1. Sofia Coppola

Sofia who along with her father, the legendary Francis Ford Coppola, is one of the few father-daughter pair who won Oscars, won hers for Best Original Screenplay for the comedy-drama Lost in Translation (2003). She was named Worst Supporting Actress and Worst New Star at the 1990 Golden Raspberry Awards, for her performance as Mary Corleone, the daughter of Michael Corleone, in The Godfather Part III (1990).
2. Faye Dunaway

Faye Dunaway won an Academy Award for Best Actress for Network (1976). She won the Razzie for Worst Actress at the 2nd Golden Raspberry Awards, for her controversial portrayal of fellow Oscar winner Joan Crawford in the camp classic, Mommie Dearest (1981). The film was nominated for nine Razzies, of which it won five.
3. Halle Berry

Halle Berry became the first African American woman to win the Academy Award for Best Actress for her performance in Monster’s Ball (2001). She won the Razzie for Worst Actress for her performance in Catwoman (2004) at the 25th Golden Raspberry Awards. The film recieved seven Razzie nominations of which it won four including Worst Picture. Berry arrived at the ceremony to accept her Razzie in person while carrying her Best Actress Oscar and parodied her Oscar speech.
4. Sandra Bullock

Sandra won the Academy Award for Best Actress for her portrayal of Leigh Anne Tuohy in The Blind Side (2009). The previous night she won her Oscar, she won the Razzie Award for Worst Actress for her performance in All About Steve (2009), making her the only actor ever to win the Oscar and Razzie in the same year.
5. Liza Minnelli

Liza won the the Academy Award for Best Actress for her legendary performance as Sally Bowles in Cabaret (1972). She won the 1988 Golden Raspberry Award for Worst Actress for her work her work in Arthur 2: On the Rocks (1988) and Rent-a-Cop (1988). Liza has the distinction of being the only performer who recieved REGOT (Razzie, Emmy, Grammy, Oscar and Tony Award).
6. Laurence Olivier

Laurence Olivier received four Academy Awards. A honorary award for Henry V (1947), a Best Actor award and one as producer for Hamlet (1948), and a second honorary award in 1979 to recognise his lifetime of contribution to the art of film. He has won two Razzies, first one for the Worst Supporting Actor for his performance in The Jazz Singer (1980) at the 1st Golden Raspberry Awards, which was held on March 31, 1981, at copywriter John Wilson’s living room, second one for the Worst Actor for his performance in legendary bad movie, Inchon (1981), at the 1983 Golden Raspberry Awards.
7. Roberto Benigni

The Italian actor won the Academy Awards for Best Actor for his performance in comedy film, Life Is Beautiful (1997). He won the Razzie for Worst Actor at the 2002 Golden Raspberry Awards for his performance in Pinocchio (2002).
8. Jared Leto

Jared Leto, the abuser of method acting, won the Academy Award for Best Supporting Actor for his performance in Dallas Buyers Club (2013). He won the Razzie Award for Worst Supporting Actor for his portrayal of fashion designer Paolo Gucci in House of Gucci (2021).
9. Eddie Redmayne

Eddie Redmayne won the Academy Award for Best Actor for his portrayal of the physicist Stephen Hawking in The Theory of Everything (2014). He won the Razzie for Worst Supporting Actor at the 2016 Golden Raspberry Awards for his performance in Jupiter Ascending (2015).
10. Tom Hooper

The British director won the Academy Award for Best Director for The King’s Speech (2010). He won two Golden Raspberry Awards for Worst Director and Worst Screenplay for the musical Cats (2019).
11. Stevie Wonder

The legendary musician won an Academy Award for Best Original Song for “I Just Called to Say I Love You”, written for The Woman in Red (1984), making him the second African-American musician to do so. He won the joint winner of Razzie for Worst Original Song for the song “Wild Wild West” with Kool Moe Dee and Will Smith, for the movie Wild Wild West (1999).
12. Ben Affleck

Ben Affleck became the youngest person ever to win an Oscar for Best Original Screenplay at age 25 for Good Will Hunting (1997), which he shared with Matt Damon. He won his second Academy Award for Best Picture for Argo (2012). He won the Razzie for the Worst Screen Couple Award with co-star Jennifer Lopez in the movie Gigli (2003).
13. Prince

The late great musician won the Academy Award for Best Original Song Score for his acting debut film Purple Rain (1984). He won two Razzies, Worst Actor and Worst Director for Under the Cherry Moon (1986) at the 7th Golden Raspberry Awards. The film also was joint Razzie winner for Worst Picture with Howard the Duck (1986).
14. Al Pacino

Al Pacino received the Academy Award for Best Actor for his role in Scent of a Woman (1992). He won the Golden Raspberry Award for Worst Supporting Actor at the 32nd ceremony for his appearance as himself in 2011 comedy film Jack and Jill.
15. Tom Hanks

Tom Hanks won two consecutive Academy Awards for Best Actor for starring as a gay lawyer suffering from AIDS in Philadelphia (1993) and the title character in Forrest Gump (1994). He won two Razzies for his performance in Elvis (2022), one the Worst Supporting Actor, the other Worst Screen Combo for his latex-laden face and bizarre accent.
16. Kim Basinger

Kim Basinger won the Academy Award for Best Supporting Actress for her performance in L.A. Confidential (1997). She won the Razzie Award for Worst Supporting Actress for her portrayal of Elena Lincoln in Fifty Shades Darker (2017).
17. Charlton Heston

Charlton Heston won the Academy Award for Best Actor for his performance in the title role of Ben-Hur (1959). He won the Razzie Award for Worst Supporting Actor at the 22nd Golden Raspberry Awards for his cameos on Cats & Dogs (2001), Planet of the Apes (2001) and his performance in Town & Country (2001).
18. Brad Pitt

Brad Pitt won two Academy Awards, first is the Academy Award for Best Supporting Actor for playing a stuntman in Once Upon a Time in Hollywood (2019), second is Academy Award for Best Picture for 12 Years a Slave (2013). He shared a Razzie for Worst Screen Couple with Tom Cruise for Interview with the Vampire (1994).
19. Marlon Brando

Even the ultimate screen legend has the ignominy of winning a Razzie, which he did in the category of Worst Supporting Actor for his performance in The Island of Dr. Moreau (1996). He won two Academy Awards for Best Actor, first for his performance as Terry Malloy in On the Waterfront (1954), second for starring as Vito Corleone in The Godfather (1972), which he refused to accept in protest of poor treatment of Native Americans in the film industry.
20. Kevin Costner

Kevin Costner won two Academy Awards for Best Picture and Best Director for starring and directing the western epic Dances with Wolves (1990). He won three Razzies for Worst Picture, Worst Actor and Worst Director for the science fiction-post-apocalyptic epic The Postman (1997).
21. James Cameron

The screen maverick has won three Oscars for Best Picture, Best Director, and Best Film Editing for Titanic (1997). He shared a Razzie for Worst Screenplay at 6th Golden Raspberry Award with Sylvester Stallone for Rambo: First Blood Part II (1985).