Birdman aka Birdman or The Unexpected Virtue of Ignorance is a 2014 black comedy directed by Alejandro G. Iñárritu that managed to win the Oscar for Best Picture a year later. A pretty bold and unconventional win, Birdman is a brilliantly-acted and aesthetically pleasing film that deserves multiple viewings to interpret its surreal undertones.

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Starring Michael Keaton as a washed-out film actor who wishes to make a comeback on Broadway, the film captures the psyche of a troubled, aging man while also dealing with his family and associates around him. While Birdman might be one of a kind, it carries on the legacy of films that deal with themes like existentialism, human respect, and magical realism.

All About Eve (1950)

Bette Davis smoking a cigarette in All About Eve

All About Eve is one of those vintage classics that still stands the test of time as a highly relevant and engaging drama. The titular Eve (Anne Baxter) is a newcomer in Hollywood who serves as a protégé to a veteran actress (Bette Davis) in the industry. But while learning the tricks of the trade, Eve becomes big enough to shadow the latter star leading to power struggles and fits of jealousy between the two.

Written and acted to perfection, All About Eve relies on melodrama to recreate a behind-the-scenes look at the world of acting and celebrity.

Ed Wood

Johnny Depp in Ed Wood

Tim Burton's stylish biopic on one of Hollywood's worst directors is a treat for fans of B-movie horror tropes. Johnny Deep gets into the skin of Ed Wood, playing an ambitious filmmaker, writer, and actor who drives his work on passion more than anything else. Most of his low-budget films end up looking goofy and sounding ridiculous, but Ed Wood never stops his cinematic pursuits.

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The real Ed Wood did get fame as the name behind movies that are "so bad they're good." Additionally, Ed Wood also deals with Wood's relationship with close friend Bela Lugosi (Martin Landau), a once-famous horror actor who struggles to make ends meet with old age.

Danny Collins

Al Pacino in Danny Collins

Al Pacino plays a popstar fading away from popularity in Danny Collins, a light-hearted comedy. Collins quits music, engrossed in his self-destructive habits of promiscuity and substance abuse. However, one night he finds an old letter addressed to him by John Lennon who tells him to never give up on his musical career. That's when Collins decides to get his life back on track and reconnect with his estranged son.

Danny Collins might not be a trailblazer of a film but its feel-good nature is good enough to address the insecurities that come with age in showbiz.

The Forty-Year-Old Version

A still from The Forty Year Old Version featuring Radha Blank on the mic

Radha Blank writes, directs, and stars in her debut film The Forty-Year-Old Version. The film is a witty yet intense story on Blank's semi-autobiographical mid-life crisis. Once a popular playwright, she now struggles with her finances while getting a new play released.

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Disappointed with the stereotypes that she faces from her white crewmembers, she ends up trying her hand at rapping, hoping that music becomes her second calling. Blanks delivers a brilliant performance while also providing vocals on some of the original rap songs on the soundtrack.

Black Swan

Natalie Portman in Black Swan

Black Swan is perhaps one of the best films to display the extents to which artists can go to achieve their goals. With flawless acting and ballet training, Natalie Portman plays a ballerina threatened by a peer who might bag a challenging role in her upcoming production.

However, true to director Darren Aronofsky's twisted mind, the film shifts genres from being an intense human drama to a dark psychological horror. Much like Birdman's Riggan, Black Swan's Nina takes her obsession with her art to toxic levels.

Pain And Glory

Antonio Banderas in Pain and Glory

Pedro Almodóvar is a Spanish auteur with several unique films in his catalog. But in Pain and Glory, he gets the most personal basing the central character on his own self. The film is a slow, introspective take on a film director's past as he recalls his childhood, relationships, and sexuality while handling his present-day chronic depression and writer's block.

While confronting his inner demons, he delves into solitude despite having plenty of fortune and fame from his career. In the end, Pain and Glory makes for an interestingly bittersweet experiment in the biopic genre.

My Dinner With Hervé

Peter Dinklage and Jamie Dornan in My Dinner With Hervé HBO

My Dinner with Hervé is a delightful HBO film that is a classical addition to the pantheon of films that deal with two characters talking, this time based on real people and a real conversation that took place. A struggling journalist (Jamie Dornan) chances upon an accidental opportunity to interview actor Hervé Villechaize (Peter Dinklage). The latter reveals through flashbacks on how he struggled to survive as a dwarf, his stardom as a supporting actor, and his eventual downfall.

The film does fall prey to several trappings of similar films but the performances of its two leads make it compelling enough to move viewers.

Kaamyaab

Kaamyaab— "successful" in English— is an Indian Hindi-language film that's streaming worldwide on Netflix. The satirical comedy spans the journey of an actor whose career just involves playing minor side-characters in films, ranging from the villain's henchman to a doctor.

Even though he's a part of major films, he never gets close to his dream of acquiring fame as a hero. While he develops a drinking habit and falls into financial loss, he finds a new purpose when he realizes he has 499 credits to his name. He tries his best to make his 500th role a major one. The film serves as a funny yet black look at Bollywood and the unsung heroes behind it.

Synecdoche, New York (2008)

Philip Seymour Hoffman in Synecdoche, New York

True to the other surreal films Charlie Kaufman has written, Synecdoche, New York is not an easy watch. The film delves deep into philosophical treatises of existentialism while focusing on a depressed playwright's life. The writer (Philip Seymour Hoffman) is struggling with a broken marriage and an experimental play as he conjures a unique plan to train his actors: He tells the cast to live in a life-size replica of New York City.

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Slowly, he begins to realize that the play is just a reflection of his tragic life, detailing all his imperfections. By the end, the lines between the play and the writer's life are so blurred that even he isn't entirely sure which is which anymore.

All That Jazz

Roy Sxhneider in a still from All That Jazz

All That Jazz finds director Bob Fosse at his self-loathing best. Fosse, who was a renowned choreographer and filmmaker, led a troubled life due to overworking, extramarital flings, and alcoholism. Fosse mixes fact with fiction to create a film that seems lively on the surface but can be quite disturbing too at times.

Roy Schneider plays the troubled showman in the lead role, a classic case of breaking typecast. Apart from dazzling musical pieces, the film gets deeply introspective while focusing on the three women in the hero's life, who try saving from imminent self-destruction.

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