10 best Alan Cumming movies: Ranked from best to worst

Ever since his film debut in 1986, Scottish actor Alan Cumming has proved his versatility by playing distinct characters across genres. Even though most moviegoers remember him for his comedic timing, the talented 60-year-old has shown that he is equally capable of nailing serious roles. Having been in the industry for almost four decades, Alan Cumming's filmography is extensive and impressive.

It is interesting to note that Alan Cumming has always found a way to bring his own flair to the characters he has played on screen, making them particularly memorable. From playing a notorious villain to a sympathetic friend, Alan Cumming is always pushing the envelope, and fans can never truly predict which avatar he will take on next, adding to the audience's anticipation.

Disclaimer: This list contains information from various sources.

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My Old School, X2, and eight other talked-about Alan Cumming movies ranked from best to worst

1) Any Day Now (2012)

This Alan Cumming movie premiered at the 2012 Tribeca Film Festival (Image via Music Box Films)

Directed by Travis Fine, this Alan Cumming starrer is based on a screenplay written by George Arthur Bloom 30 years prior to its release. Cumming plays Rudy Donatello, a struggling musician and drag performer. He becomes close to Garret Dillahunt's Paul Fliger, a closeted district attorney.

When Rudy sees a young boy with Down syndrome in need of a responsible guardian, he steps up to provide for him. He seeks help from Paul in the matter, but just when things seem to be going smoothly, complications start to bubble up.

Alan Cumming is endearing and likable as Rudy. His evolving relationship with Paul and determination to protect Isaac Leyva's Marco feels genuine, prompting the audience to root for him. Instead of a Hollywood-style ending, Fine's movie ends on a realistic note that lingers with the audience.

Where to watch: Prime Video, Apple TV+, and Tubi

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2) My Old School (2022)

This documentary is engaging from start to finish (Image via Magnolia Pictures)

This documentary starring Alan Cumming is focused on the Brandon Lee scandal. The bizarre incident took place at Bearsden Academy Secondary School. 32-year-old Brian MacKinnon assumed the name of Brandon Lee and posed as a 16-year-old. He enrolled as a fifth-year student at the school and was well-liked by his peers and professors, but his true identity soon came to the surface.

Director Jono McLeod was able to interview MacKinnon for the film, but he refused to show his face on screen. Therefore, Alan Cumming appears as MacKinnon's avatar. The lip sync is so smooth that viewers tend to forget it is not really Cumming saying the words.

McLeod's My Old School shines because of its clever formatting. The interviews are interesting, the animation is eye-catching, and there are enough new reveals to keep viewers invested till the end.

Where to watch: MUBI, Apple TV+, and Prime Video

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3) Sweet Land (2015)

Sweet Land is heartwarming and poignant (Image via Official Movie Website)

Alan Cumming fans who enjoy period dramas should make a point to add this underrated gem to their watchlist. Directed by Ali Selim, it is based on Will Weaver's story titled A Gravestone Made of Wheat. Elizabeth Reaser plays Inge Altenberg, who travels from Norway to rural Minnesota to enter into an arranged marriage with Tim Guinee's Olaf Torvik, a Norwegian farmer.

In the movie, Alan Cumming plays Frandsen, a friend of Olaf. Interestingly enough, the character was specifically written for the actor, as he was one of the early supporters of the movie. As expected, Alan Cumming didn't disappoint and delivered a memorable performance, matching the rest of the talented cast.

On the surface, the narrative of Sweet Land seems simple, but it has plenty of thought-provoking moments that viewers will find gratifying.

Where to watch: Prime Video and Apple TV+

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4) The Anniversary Party (2001)

The Anniversary Party thrives on a realistic screenplay (Image via Alan Cumming Official Website)

No quintessential Alan Cumming list can be complete without this title, as it marks his feature directorial debut. However, it must be kept in mind that he shares his achievements with Jennifer Jason Leigh. In addition to their directorial responsibilities, both of them also star in the movie.

They play Sally Nash and Joe Therrian, a Hollywood couple who were going through a period of separation but reconciled shortly before their sixth wedding anniversary. Unfortunately, the celebration party takes a turn when hidden confessions and secrets come out.

The Anniversary Party explores the other side of celebrities, the side that stays hidden when the cameras are flashing. The realistic characters are complemented by clever dialogue and believable plot progressions, resulting in entertaining cinema.

Where to watch: Prime Video and Apple TV+

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5) Battle of the Sexes (2017)

Tennis fans shouldn't miss out on this gem starring Alan Cumming (Image via 20th Century Studios)

Like My Old School, this Alan Cumming movie is also based on real events. Directed by Valerie Faris and Jonathan Dayton, it explores how the 1973 tennis match between Billie Jean King and Bobby Riggs came to be, and the impact it had on society as a whole.

In Battle of the Sexes, Emma Stone and Steve Carell portray tennis legends King and Riggs, respectively. Alan Cumming portrays Cuthbert Tinling, aka Ted, an openly gay fashion designer who designs King's outfit for the highly debated match. Except for the hair, Cumming perfectly captures Ted's ingenuity and his flair for creating iconic tennis dresses for Wimbledon champions.

The narrative offers a deep dive into both players, their relationships and insecurities, and also tackles social issues like gender inequality, prejudices in sport, and more.

Where to watch: Disney+, Prime Video, and Apple TV+

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6) X2 (2003)

X2 received a lot of praise for its narrative and special effects (Image via 20th Century Studios)

Directed by Bryan Singer, X2 is the second installment in the X-Men film series. Based on the graphic novel God Loves, Man Kills, the movie shows the X-Men teaming up with the Brotherhood of Mutants to put a stop to Colonel William Stryker's genocidal plan aimed at destroying every mutant on Earth.

It boasts an ensemble cast that features the likes of Patrick Stewart, Ian McKellen, Hugh Jackman, Halle Berry, Alan Cumming, and more. Cumming plays Kurt Wagner, more commonly known as Nightcrawler. The methodical actor studied comic books and illustrations of the character to ensure that his portrayal was accurate and thorough.

The clashing dynamics and differences in opinions between the two teams, who have no choice but to work together towards a common goal, are among the main highlights of this movie.

Where to watch: Disney+ and Hulu

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7) Goldeneye (1995)

Goldeneye is the seventeenth title in the James Bond series (Image via James Bond Official Website)

This is the first James Bond movie to star Pierce Brosnan in the titular role. Directed by Martin Campbell, the movie is based on the characters of Ian Fleming but doesn't follow the storyline of any of the written novels. In the movie, Bond has to stop the Janus crime syndicate from getting their hands on GoldenEye, a clandestine satellite weapon.

Alan Cumming plays Boris Grishenko, a computer programmer who turns out to be one of the baddies. He has a couple of iconic lines in the movie that have attained meme status over the years. In terms of ferocity, the character doesn't match the movie's main villains, but he is still well remembered as a Bond villain because of the horrific way he dies, frozen solid in liquid nitrogen.

Where to watch: Prime Video and Apple TV+

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8) Josie and the Pussycats (2001)

Josie and the Pussycats is perfect for viewers who want a no-brainer (Image via Universal Pictures)

The name of this title featuring Alan Cumming will feel quite familiar to Archie Comics fans because it is based on well-known characters from the series. In this musical comedy by Harry Elfont and Deborah Kaplan, Rachael Leigh Cook, Tara Reid, and Rosario Dawson play Josie McCoy, Melody Valentine, and Valerie Brown, respectively. All of them are part of a band called The Pussycats.

The band is discovered by Alan Cumming's Wyatt Frame, a notorious promoter who recruits young bands for MegaRecords. However, the three protagonists are unaware that MegaRecords puts subliminal messages into the music they produce. Wyatt may not rank high on the list of intimidating movie villains, but he is still memorable thanks to Cumming's perfectly-timed slapstick comedy.

Where to watch: Hulu, Apple TV+, and Roku

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9) Spy Kids (2001)

Spy Kids will appeal to young children and families (Image via Miramax)

This Alan Cumming starrer made a splash when it was released back in the day because it was one of the first spy movies specifically targeted towards a younger audience. Directed by Robert Rodriguez, it stars Antonio Banderas, Alexa PenaVega, Daryl Sabara, Alan Cumming, and more.

PenaVega and Sabara play Carmen and Juni Cortez, who have no idea that their parents are actually spies. But things come out in the open when their parents are kidnapped, and they have to come up with a plan to save them. Alan Cumming plays Fegan Floop, a television host who turns people into disfigured creatures called "Fooglies" for his show.

For adults, Fegan Floop is a rather tame villain, but he gets the job done for kids, which is probably what Cumming was aiming for anyway.

Where to watch: HBO Max, Apple TV+, and Prime Video

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10) Spice World (1997)

This is a must-watch for fans of the Spice Girls (Image via Official Facebook Page)

Music fans around the world have heard of the Spice Girls. After all, they are the best-selling girl group of all time. This movie came out at the height of their popularity. Directed by Bob Spiers, it follows a series of fictional events leading up to a concert at the Royal Albert Hall in London. The members of the girl group play themselves on screen.

This movie, considered a cult classic, stars Alan Cumming as Piers Cuthbertson-Smyth, who stalks the girls, with a camera crew in tow, in the hopes that he will be able to use them as subjects for his next big project.

Now, Piers isn't the kind of character that one would write home about. After all, he is simply taping young girls getting into silly shenanigans, but the over-the-top gravitas with which he approaches his subjects certainly adds to the humor of the movie.

Where to watch: Plex

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Alan Cumming has had an illustrious career, and cinephiles will always remember him for playing iconic and intriguing characters in these popular movies.