20 best movies like Delivering Milo (2001)

Gloria is a free-spirited divorcée who spends her days at a straight-laced office job and her nights on the dance floor, joyfully letting loose at clubs around Los Angeles. After meeting Arnold on a night out, she finds herself thrust into an unexpected new romance, filled with both the joys of budding love and the complications of dating, identity, and family.

The Wild West, circa 1870. Samuel Alabaster, an affluent pioneer, ventures across the American frontier to marry the love of his life, Penelope. As his group traverses the west, the once-simple journey grows treacherous, blurring the lines between hero, villain and damsel.

In the Australian Outback, the Carmody family--Paddy, Ida and their teenage son Sean--are sheep drovers, always on the move. Ida and Sean want to settle down and buy a farm. Paddy wants to keep moving. A sheep-shearing contest, the birth of a child, drinking, gambling and a race horse will all have a part in the final decision.

Despite grumpy 59 year-old Ove being deposed as president of his condominium association, but he keeps looking over the neighbourhood with an iron fist. When pregnant Parvaneh and her family move into the terraced house opposite Ove and she accidentally back into Ove’s mailbox, it sets off a series of unexpected changes in his life.

Middle-aged and divorced, Wilson finds himself lonely, smug and obsessed with his past.

Vignettes weaving together the stories of six individuals in the old West at the end of the Civil War. Following the tales of a sharp-shooting songster, a wannabe bank robber, two weary traveling performers, a lone gold prospector, a woman traveling the West to an uncertain future, and a motley crew of strangers undertaking a carriage ride.

A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

Single mom Laura, along with her awkward 14 year-old son Henry is forced to drive Jack, her estranged, care-free pot dealing father across country after he's kicked out of yet another nursing home.

Miranda Presley moves from New York to Nashville to become a songwriter. At an unsuccessful audition she meets James Wright, a promising newcomer. After only a few days they marry but start to quickly regret it.

Ned (Liev Schreiber) is in the throes of a mid-life crisis. His work as a writer on an outrageous, semi-pornographic TV show is less than satisfying. His fifteen year old son has just told him he is gay and his eleven year old is afraid of, well pretty much everything. When his wife, Jeannie (Helen Hunt), moves her sick and embittered father (Brian Dennehy) from Detroit into their home in NY, it puts added stress on an already strained marriage. And when a sexy female co-worker (Carla Gugino) puts the moves on Ned, the temptation sends him spiraling. EVERY DAY is about one family's struggle to survive the unexpected curve-balls that are simply part of real life; aging and death; commitment and freedom; love and acceptance. It's an uncompromising look at an ordinary family making an extraordinary journey towards themselves and towards each other.

A washed up Vegas lounge singer, Jack Satin (Hamilton von Watts), has no money, no job, and delusional aspirations of fame. When Jack is forced to leave Vegas, he packs up his old Cadillac and hits the road for Atlantic City. But his car dies in the desert and Jack is left stranded in the small town of Lost Springs. There, Jack meets jazz legend turned mechanic, Doc Bishop (Robert Guillaume), who helps him with his car trouble. Although Jack is far from the stage, he begins to find himself feeling at home in the small town. When he meets local bar owner, Lauren Wells (Melissa Joan Hart), Jack starts to see there is more to life than chasing fame and fortune. Doc encourages Jack to explore his true love of music, while Lauren provides the audience he has always wanted. But as Jack realizes this town has more to offer him than the bright lights of the big city, his Vegas past catches up with him -- what unfolds is comedy at the crossroads of life.

A woman struggles to escape the clutches of her overbearing, co-dependent mother, while gradually falling for a sexy, sophisticated attorney.

A runaway couple go on an unforgettable journey from Boston to Key West, recapturing their passion for life and their love for each other on a road trip that provides revelation and surprise right up to the very end.

Good natured Reverend Henry Biggs finds that his marriage to choir mistress Julia is flagging, due to his constant absence caring for the deprived neighborhood they live in. On top of all this, his church is coming under threat from property developer Joe Hamilton. In desperation, Rev. Biggs prays to God for help - and help arrives in the form of an angel named Dudley.

Lucy, a small-town girl from Ohio, discovers the delightfully bizarre films of legendary filmmaker Federico Fellini and sets off on a journey across Italy to find him.

Ingrid becomes obsessed with a social network star named Taylor Sloane who seemingly has a perfect life. But when Ingrid decides to drop everything and move west to be Taylor's friend, her behaviour turns unsettling and dangerous.

When George and her colleagues get a new boss whose focus is on moving souls quickly and enjoying life without consequences, the team begins to break the strict reaper rules. While her friends fall victim to their desires for money, success, and fame, George breaks another rule by revealing her true identity to her living family.

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or if their lives are actually more flawed than they appear.

Claire is a midwife and has devoted her life to others. At a moment when she is preoccupied by the imminent closure of the maternity clinic where she works, her life is further turned upside down when Béatrice, her father's former mistress, turns up on the scene. Béatrice is a capricious and selfish woman, Claire's exact opposite.

With a new iPhone, an apartment near the Grove, and a comfortable bank account left to her by her beloved late husband, Marnie Minervini has happily relocated from New Jersey to Los Angeles to be near her daughter Lori, a successful (but still single) screenwriter, and smother her with motherly love. But when the dozens of texts, unexpected visits, and conversations dominated by unsolicited advice force Lori to draw strict personal boundaries, Marnie finds ways to channel her eternal optimism and forceful generosity to change the lives of others - as well as her own - and find a new purpose in life.

A widowed aeronautics engineer, who has lost his job, travels with his son hopping freight trains from Moscow to Koktebel, a town by the Black Sea, to start a new life with the father's sister.

Beatriz, an immigrant from a poor town in Mexico, has drawn on her innate kindness to build a career as a health practitioner. Doug Strutt is a cutthroat, self-satisfied billionaire. When these two opposites meet at a dinner party, their worlds collide, and neither will ever be the same.

Eloise, having been relieved of maid of honor duties after being unceremoniously dumped by the best man via text, decides to attend the wedding anyway – only to find herself seated with five fellow-unwanted guests at the dreaded Table 19.

Antoine and Kenny Tyler are NCAA college basketball players, and Antoine is the star. Suddenly Antoine dies of heart attack and Kenny has to fill his shoes as leader of team. Some time later, Antoine returns as a ghost and helps Kenny in game and in life, but Kenny changes in the process and doesn't quite like it.

A working girl from New Jersey looks for love with a fast-lane Manhattan salesman from Queens.

A regular guy struggles with a repressive home and professional life, as well as making amends for the trouble his free-spirited brother and sister cause about town.

Irresponsible party girl Maggie (Cameron Diaz) is kicked out of her father's (Ken Howard) and stepmother's (Candice Azzara) home, where she lives for free, and is taken in by her hard-working sister, Philadelphia lawyer Rose (Toni Collette). After Maggie's disruptive ways ruin her sister's love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.

Four girlfriends take a trip to New Orleans for an annual festival and, along the way, rediscover their wild sides and strengthen the bonds of sisterhood.

A lady has her prim and proper life turned upside down after discovering her husband's affair.

A satirical drama reflecting our times — about the sense of community, moral courage and the affluent person’s need for egocentricity in an increasingly uncertain world.

A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.

A young woman leaves the city to return to her hometown in the countryside. Seeking to escape the hustle and bustle of the city, she becomes self-sufficient in a bid to reconnect with nature.

Jason Staebler lives on the Boardwalk and fronts for the local mob in Atlantic City. He is a dreamer who asks his brother David, a radio personality from Philadelphia, to help him build a paradise on a Pacific Island, which might be just another of his pie-in-the-sky schemes. Inevitably, complications begin to pile up.

Straight out of Jersey comes Patricia Dombrowski, a.k.a. Killa P, a.k.a. Patti Cake$, an aspiring rapper fighting through a world of strip malls and strip clubs on an unlikely quest for glory.

A young man is rocked by two announcements from his elderly father: that he has terminal cancer, and that he has a young male lover.

It's Hollywood, 1958. Small town beauty queen and devout Baptist virgin Marla Mabrey, under contract to the infamous Howard Hughes, arrives in Los Angeles. At the airport, she meets her driver Frank Forbes, who is engaged to be married to his seventh grade sweetheart and is a deeply religious Methodist. Their instant attraction not only puts their religious convictions to the test, but also defies Hughes' number one rule: No employee is allowed to have any relationship whatsoever with a contract actress. Hughes' behavior intersects with Marla and Frank in very separate and unexpected ways, and as they are drawn deeper into his bizarre world, their values are challenged and their lives are changed.

An aging Latin lover gets dumped by his sugar mama and must fend for himself in a harsh world.

A woman at a crossroads traveling to Cannes along with her successful film producer husband, finds herself on a two-day road trip with his business associate. What follows is a carefree journey replete with diversions involving picturesque sites, fine food and wine, humor, wisdom and romance - reawakening Anne's senses and a new lust for life.

A man is reluctant to tell his fiancee that his parents, uncle and brother are dwarfs.

Maggie's plan to have a baby on her own is derailed when she falls in love with John, a married man, destroying his volatile marriage to the brilliant and impossible Georgette. But one daughter and three years later, Maggie is out of love and in a quandary: what do you do when you suspect your man and his ex wife are actually perfect for each other?

Benjamin has lost his wife and, in a bid to start his life over, purchases a large house that has a zoo – welcome news for his daughter, but his son is not happy about it. The zoo is in need of renovation and Benjamin sets about the work with the head keeper and the rest of the staff, but, the zoo soon runs into financial trouble.

Based on the John Irving novel, this film chronicles the life of T S Garp, and his mother, Jenny. Whilst Garp sees himself as a "serious" writer, Jenny writes a feminist manifesto at an opportune time, and finds herself as a magnet for all manner of distressed women.

Aging screenwriter Felix Bonhoeffer has lived his life in two states of existence: in reality and his own interior world. While working on a murder mystery script, and unaware that his brain is on the verge of implosion, Felix is baffled when his characters start to appear in his life, and vice versa.

When a chance encounter brings together the cynical Dell and the quick-witted Kimberly, the stage is set for a tempestuous love affair that unfolds like a puzzle. As the film zigzags back and forth in time-from a meteor shower in LA, to an encounter in a Paris hotel room, to a fateful phone call-an unforgettable portrait of a relationship emerges.

A young boy whose parents just divorced finds an unlikely friend and mentor in the misanthropic, bawdy, hedonistic, war veteran who lives next door.

The true story of the 1973 tennis match between World number one Billie Jean King and ex-champ and serial hustler Bobby Riggs.

After her fiance is falsely imprisoned, a pregnant African-American woman sets out to clear his name and prove his innocence.

Anger rages in Philip as he awaits the publication of his second novel. He feels pushed out of his adopted home city by the constant crowds and noise, a deteriorating relationship with his photographer girlfriend Ashley, and his own indifference to promoting the novel. When Philip's idol Ike Zimmerman offers his isolated summer home as a refuge, he finally gets the peace and quiet to focus on his favorite subject: himself.

Divorced and demoralised, Amy Minsky’s prospects look bleak when she is condemned to move back in with her parents at the age of 35. Everyone wants to help but, as her patience level with advice is plummeting, a bold teenage boy enters her life, igniting her last bit of self-esteem.