If you enjoyed the quirky, heartfelt, and slightly awkward humor of 'Cyrus' (2010), you're in for a treat! This article explores 10 movies and TV shows that capture the same blend of offbeat comedy, emotional depth, and unconventional relationships. Whether you loved the dynamic between John, Molly, and Cyrus or simply appreciate indie films with a unique charm, this list will guide you to your next favorite watch.

Flirting with Disaster (1996)
Description: This shares with 'Cyrus' a mix of uncomfortable humor and family dysfunction. Both films feature protagonists on personal journeys that reveal their emotional immaturity. The ensemble casts and awkward social situations create similar comedic tension, though 'Flirting' is more overtly farcical.
Fact: Features an early Ben Stiller performance. The film includes three different sets of parents. Director David O. Russell improvised much of the dialogue.


The Squid and the Whale (2005)
Description: Like 'Cyrus', this film examines dysfunctional family dynamics with a mix of humor and pathos. Both movies feature uncomfortable parent-child relationships and explore themes of emotional immaturity in adults. The raw, confessional tone and awkward humor are similar, though 'The Squid and the Whale' is more autobiographical.
Fact: The film is loosely based on writer/director Noah Baumbach's childhood. Shot in just 23 days on a small budget. Features early performances from Jesse Eisenberg and Owen Kline.


Margot at the Wedding (2007)
Description: This film shares with 'Cyrus' an exploration of family dysfunction and emotionally stunted adults. Both feature uncomfortable social interactions and a blend of comedy and drama. The naturalistic dialogue and focus on flawed characters trying to connect are similar, though 'Margot' has a more acerbic tone.
Fact: Nicole Kidman and Jennifer Jason Leigh play sisters in the film. Director Noah Baumbach wrote the role specifically for Kidman. The film was shot on Long Island in just 32 days.


The Savages (2007)
Description: Like 'Cyrus', this film deals with emotionally stunted adults facing family responsibilities. Both blend comedy and drama in their portrayal of dysfunctional relationships. The films share a similar naturalistic style and focus on characters who are simultaneously sympathetic and frustrating.
Fact: Philip Seymour Hoffman and Laura Linney play siblings. The film was shot in 30 days. Writer/director Tamara Jenkins drew from her own experiences with aging parents.


The Kids Are All Right (2010)
Description: Like 'Cyrus', this film explores unconventional family dynamics with humor and heart. Both deal with the intrusion of an outsider into a family unit and the resulting tensions. The naturalistic performances and blend of comedy and drama are similar, though 'Kids' has a more optimistic tone.
Fact: Mark Ruffalo's character was originally written for Philip Seymour Hoffman. The film was shot in just 23 days. Annette Bening learned to play Joni Mitchell songs on guitar for her role.


Greenberg (2010)
Description: Similar to 'Cyrus' (2010), 'Greenberg' is a character-driven indie dramedy that explores themes of loneliness, personal dysfunction, and awkward human connections. Both films feature protagonists struggling with midlife crises who form complicated relationships with younger people. The films share a similar naturalistic dialogue style and uncomfortable humor.
Fact: Ben Stiller plays against type as the socially awkward Greenberg. The film marked Greta Gerwig's breakout role. Director Noah Baumbach based the character of Greenberg on people he knew in the New York music scene.


The Skeleton Twins (2014)
Description: Like 'Cyrus', this film explores dysfunctional family relationships with a mix of humor and melancholy. Both feature characters struggling with emotional issues who use humor as a defense mechanism. The balance between comedy and drama is similar, with both films finding humor in dark situations.
Fact: Bill Hader and Kristen Wiig are real-life friends. The lip-sync scene was improvised. The film was shot in just 22 days.


Young Adult (2011)
Description: This shares with 'Cyrus' a focus on emotionally immature protagonists. Both films blend comedy and pathos in their portrayal of socially awkward characters. The uncomfortable humor and examination of personal dysfunction are similar, though 'Young Adult' has a darker edge.
Fact: Charlize Theron gained 15 pounds for the role. Director Jason Reitman and writer Diablo Cody reteamed after 'Juno'. The film was shot in just 30 days.


The One I Love (2014)
Description: Like 'Cyrus', this film explores relationship dynamics with an offbeat, sometimes uncomfortable humor. Both deal with the complexities of human connection and personal identity. The blend of comedy and psychological drama is similar, though 'The One I Love' has a more surreal premise.
Fact: The film's twist was kept secret from audiences. Mark Duplass also served as an executive producer. The entire film was shot at one house location.


Obvious Child (2014)
Description: This shares with 'Cyrus' a blend of awkward humor and emotional honesty. Both films deal with personal growth through uncomfortable situations. The naturalistic performances and indie sensibility are similar, though 'Obvious Child' tackles more controversial subject matter.
Fact: Jenny Slate's stand-up in the film is her own material. The film was shot in just 19 days. Director Gillian Robespierre expanded the film from her 2009 short.
