Nothing beats the job security of appearing on a weekly multi-season sitcom. Securing a recurring role on a hit comedy show like The Office, Friends, Seinfeld, or Parks & Recreation could mean a lifetime of no work even after the show’s finale comes around. Despite this, the worst nightmare of some sitcom actors is being eternally straddled by one singular character for the rest of their lives. These actors fear that, after their big break, they’ll be typecast as the same character over and over again. This is a valid concern, as this has happened to countless sitcom alums, but in rare cases, it leads to absolute brilliance.
In 2006, a fresh off of Friends Jennifer Aniston fell victim to the perils of typecasting. The now-prolific comedy movie actor had to fight an uphill battle to secure her relevance outside of the television world. From indies to animated films to the rom-coms that would become her bread and butter later in life, Aniston fought and clawed her way to the top, and it all started with the dreaded question, “Can you play a Rachel Green-esque character?” The result of this is 2006’s Friends With Money, a breezy and laid-back romantic relationship comedy that features a surprisingly star-studded cast for a quaint indie film. The film has been largely forgotten by comedy fans, but undoubtedly deserves to be remembered.
What is Friends With Money About?
Friends with Money Jennifer Aniston Frances Mcdormand Joan Cusack Catherine KeenerImage Via This is That
Friends With Money is one of many highly underrated indie films from the mid-2000s. This era was completely dominated by franchise fever and animated films, leading to countless gems being left undiscovered. The film was directed by Nicole Holofcener, who has continuously made a name for herself as one of the most interesting independent directors in the feature film scene. Holofcener is most known for her collaborations with Julia Louis-Dreyfus, including 2023’s You Hurt My Feelings, and 2013’s James Gandolfini tour de force, Enough Said. Prior to finding who many consider her muse, Holofcener was still pumping out subtle, offbeat, and thought-provoking dramas on a regular basis.
When compared to her other films, like The Land of Steady Habits and You Hurt My Feelings, Friends With Money is highly uneventful and light-hearted, but that’s what makes it such a breath of fresh air. There is aimlessness to the events in this satirical relationship comedy that will feel not like a film, but like a peek into the lives of some old friends.
While the film has an aimless vibe, there is still a discernible plot to follow. The film primarily follows Olivia (Jennifer Aniston), a former teacher who, after losing her job, has entered something of a downward spiral. Strapped for money, Olivia picks up a job cleaning houses to make ends meet, but it ends up only heightening her self-worth issues. She’s surrounded by three longtime friends, Jane, Franny, and Christine, all of whom are financially stable, married, and overbearing when it comes to Olivia’s life.
The film tracks not only Olivia’s search for love and stability in life, but also Franny, Christine, and Jane’s struggles despite having all of that. These four women, and the rotating ensemble cast of husbands, boyfriends, and friends, recklessly navigate marriage, aging, money, and their own egos. Their naturalistic conversations and spats expose the bubbling tensions hidden under their seemingly picture-esque lives. The film seeks to point out that, regardless of financial stability or relationship status, everyone has the same problems, and no dollar or cent can fix that.
Friends With Money, thanks to Nicole Holofcener’s soft touch, moves with empathy and understanding, and is all the better for it. Olivia’s aimlessness and misguided behavior serves as a brilliantly constructed counterpoint to the mundane monotony of her friends’ upper-middle-class suburban lives. The film, aside from its thesis about money not directly causing happiness, also muses on friendship and how pointless comparisons and unspoken resentment can manifest in the real world.
This Jennifer Aniston-led film deserves to be remembered not only for its sharp comedy and screenplay (which is also credited to Holofcener), but also for the poignant lessons it teaches. Friends With Money is a subtle, but smart, character study that seamlessly blends humor and melancholy into a pitch-perfect treatise on the stresses of womanhood and the repetitiveness of life.
Friends With Money Feels Like a Lost Friends Filler Episode
The connection between Friends With Money and Friends goes far deeper than the word “Friends.” The film and television show have a litany of similarities that range from the film’s easygoing vibe, all the way to the construction of the film’s main character.
Courtney Cox was originally supposed to play Rachel Green in Friends, but asked to play Monica instead, leaving the door open for Jennifer Aniston to take the role.
While the character of Rachel Green in Friends would develop into something real and fully fleshed out over the course of the hit show’s ten seasons, she was an entirely different beast upon the show’s pilot airing. At the beginning of David Crane’s incredible sitcom, Rachel Green could only be described as spoiled, hopeless, and aimless in the real world. Friends With Money’s Olivia isn’t so different. Olivia is a wayward soul lost in life, who has found herself completely devoid of love and passion, especially when compared to the seemingly idyllic lives lived by her friends. Jennifer Aniston returns to her roots with her powerhouse performance as Olivia, and, as viewers will see, she didn’t lose a single step.
Images of Phoebe, Ross and Joey in Friends
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Friends With Money also relates to the world of television in a way completely unrelated to the plot of Friends. The aforementioned easy breezy aimlessness that fills the runtime of the film will feel familiar to sitcom fans. While most films, especially romantic comedies, will feature high-stakes drama and impassioned pleas of romance, Friends With Money is completely devoid of that. The film instead invokes the feeling of a sitcom filler episode, with relationship developments that feel like minor updates in a larger story.
Nicole Holofcener’s film is an entry into the small but mighty lineage of cozy and uneventful rom-coms. Instead of the passion and glorified romance of the average adult rom-com, Friends With Money instead has small moments of frustration, realizations of incompatibility, and arguments that will feel ripped out of the viewer’s own personal life. The film gives credence and attention to issues that audience members will forget they even have, and manages to make everyone feel seen in the process.
Friends With Money Received Mixed Reviews
Friends With MoneyImage Via This is that
Nicole Holofcener has suffered from complicated critical receptions throughout her entire career, but none have been weirder than Friends With Money. The film was immediately a hit with critics, scoring big wins (Frances McDormand for Best Supporting Actress) at award shows like the Independent Spirit Awards, and garnering positive reviews across the board on various platforms. As of April 2025, Friends With Money has a 72% fresh rating on Rotten Tomatoes from 154 reviews, with many critics praising the film’s lead performances, sharp comedy, and intense relatability.
IMDb Score
Tomatometer
Popcornmeter
Letterboxd Score
5.8/10
72%
40%
2.7/5
In terms of audience reception, Friends With Money has a completely different story. It seems to be true in almost every case, but Nicole Holofcener’s brand of uneventful relationship drama seems to work better with those who made movie-watching their job. Friends With Money has a frighteningly low rating of 2.7/5 from viewers on Letterboxd, and an equally frustrating 5.8/10 on IMDb. As of April 2025, Friends With Money has a rotten score of 40% on Rotten Tomatoes from audiences, with many stating that the film completely lacks stakes and a satisfying climax.
