At 67, Whoopi Goldberg is one of the few actors who have won four of the most prestigious American film awards in Hollywood (via Insider). This includes an Oscar, a Grammy, a Tony, and an Emmy — aka EGOT. Her well-decorated career is owed to her brilliant acting and her effortless ability to inspire humor. Despite being completely different from her reflective 1985 breakthrough role in Steven Spielberg’s The Color Purple, Goldberg’s exceptional talent for comedy demonstrated that she possessed a distinctive and compelling range that has cemented her as a titan in the film industry.
In recent years, Goldberg’s cinema accolades have been shrouded by her socio-political views on television talk shows. However, it is impossible not to momentarily revere one of Hollywood’s highest-paid actors, who cracked audience’s ribs time and time again with her endearing characters that helped shape the comedy genre. From Burglar, Fatal Beauty, Sister Act, The Associate, and the Oscar-winning performance in Ghost, Goldberg’s comedy films (and roles) stand out in the memory. Before the highly anticipated Sister Act 3 joins the list, here are Whoopi Goldberg’s top 10 funniest movies across four decades of filmography.
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10 Fatal Beauty (1987)
MGM
In this enjoyable crime-comedy from filmmaker Tom Holland (who also directed Fright Night and Child’s Play before Fatal Beauty), Goldberg plays a detective who doesn’t follow the rules. The movie was derided as a Beverly Hills Cop rip-off at the time of its 1987 release, and was not considered to be a commercial or critical success.
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It does, however, have its humorous moments, with Goldberg getting to show off her comedic flair as a cop who dons various disguises to catch the bad guys, much like Fletch did. The movie also shows her overcoming the taunts and insults from her male coworkers, demonstrating a strong woman character who can look after herself.
9 Boys on the Side (1995)
Warner Bros.
When Boys on the Side was first released, it generated considerable controversy. Drew Barrymore, Mary-Louise Parker, and Goldberg play friends who meet by chance. After killing an abusive lover accidentally, the sisters find themselves on the run.
The women develop a close bond as they journey across the nation, and it is later discovered that one of them is HIV-positive. Using women to convey a tale about HIV in 1995 was contentious and shocking because society had previously believed that the disease primarily affected gay males.
8 Made in America (1993)
Goldberg had a major box office hit with Made in America. She portrays Sarah Mathews, a lady who became pregnant thanks to an unidentified sperm donor and learns that her adult daughter has found her biological father. Sarah is shocked to learn that the Black donor she had specifically sought is instead a brash, conceited white auto salesperson. This charming, likable, and occasionally very amusing cultural clash comedy skillfully weaves themes of parenthood, identity, and race together.
7 Ghost (1990)
Paramount Pictures
Despite almost not being cast in Ghost, Goldberg won the Best Supporting Actress Oscar for her performance. In the movie, she portrays con artist Oda May Brown, who says she can communicate with ghosts. She can hear the voice of a deceased man until, one day, he instructs her to notify his wife because she is in danger. Ghost is well-known for its pottery scene in which Goldberg’s iconic line is delivered: “Molly, you in danger, girl.”
6 The Associate (1996)
Hollywood Pictures
Unjustly, The Associate has been dismissed as a lesser retelling of classic cross-dressing comedies like Mrs. Doubtfire and Tootsie. It undoubtedly has some parallels, but it also stands out sharply from the crowd, probably best illustrated by the fact that this isn’t just any woman claiming to be a guy — she’s also a Black woman pretending to be a white man.
The movie touches on various topics, including race and how gender and skin color may affect job advancement, as well as the place of women in power-hungry, male-dominated corporate circles. Thanks to Goldberg’s inherent sense of humor, it nonetheless succeeds in becoming a feel-good comedy.
5 Soapdish (1991)
Hollywood Road Films
In the hilarious and insightful tale about life on soap opera TV, Soapdish, a fantastic ensemble cast can’t keep Goldberg in the shadows. As usual, Sally Field, Kevin Kline, and a huge list of other actors — including Teri Hatcher, Robert Downey Jr., Cathy Moriarty, Elisabeth Shue, and Carrie Fisher — perform admirably.
4 Corrina, Corrina (1994)
New Line Cinema
Corrina, Corrina centers on the unanticipated connection that develops between a white widower and his Black servant in 1950s Los Angeles. The film’s appeal comes from its moving depiction of motherhood and family amid cultural and political upheaval, which is set against the backdrop of racial tensions in the United States during the Civil Rights period. Goldberg exhibits charming, frail, and natural reserve in this situation. And despite her character’s unfortunate stereotypes and discrimination, she maintains her capacity for humor.
3 Sister Act 2: Back in the Habit (1993)
Touchstone Pictures
The follow-up to Goldberg’s hugely successful Sister Act, Sister Act 2: Back in the Habit, is a bit heavy-handed, a bit sappy, and strains your ability to suspend disbelief, but the songs are fantastic, and the finale feels right. Naturally, because it features Goldberg’s most well-known character, and there is an immediate connection between the audience and the movie as a result of the actor returning to the part with such comfort.
Goldberg’s impressive vocal range brings music to the classroom to help a group of rowdy kids get back on the right track through music, taking its cues from movies like To Sir, With Love, though with added song and dance routines.
2 Sister Act (1992)
Buena Vista Pictures
This comedy-musical has lots of funny moments and similarly excellent music. Deloris, a nightclub singer in Reno, is placed under witness protection after she witnesses a mob hit. As a nun at a somnambulant convent where both the nuns and the congregation have lost the joy and spirit of worship, she is living her “new life.” Deloris must reimagine the church to make it more pertinent in the fast-evolving 1990s. Although fans and critics well received Sister Act, its follow-up is what audiences remember the most.
1 Jumpin’ Jack Flash (1986)
20th Century Studios
In this comedy-drama, Terry Dolittle is a funny but dissatisfied office worker pushed into the world of spies and international espionage. Jumpin’ Jack Flash is a severely undervalued movie in which Goldberg shines. With a focus on Goldberg’s fish-out-of-water experience and a cast of funny supporting players, director Penny Marshall ties this film together, making it an 80s classic.
Goldberg uses Jumpin’ Jack Flash as her stage to perform. A year after being nominated for an Oscar for her work in Steven Spielberg’s The Color Purple, the actress was still mostly unknown to theatergoers. But it was about to change in 1986. The movie allowed her to show off her vibrant personality and loud, frequently cynical sense of humor, which would later help establish the Goldberg “brand”.
