Film
The Trouble with Angels
- Comedy
- Light-hearted
A 1966 comedy about two mischievous girls at a Catholic boarding school who drive the nuns to distraction with pranks, only to discover unexpected depth in their strict teachers. It's warm and funny without being mean-spirited, balancing adolescent chaos against genuine affection. Perfect for anyone who loves ensemble comedies or stories about unlikely understanding across generational lines.
Should you watch it?
Watch it if you like light, episodic school comedy where mischief drives the story and the characters are more fun than the plot, the kind of gentle rebellion that stays mostly harmless.
Skip it if you want sharp, fast jokes or a story with a clear spine; this ambles, leans sentimental, and keeps its mischief small-scale.
What it asks of you: A relaxed 112 minutes with little strain on attention; it sits lightly, drifting from one bit of mischief to the next, and asks only for an easygoing mood.
Not sure? Find tonight's pick in a minute.
If you liked this
Singin' in the Rain1952
Pure joyful energy from start to finish, with a young ensemble cast and that same spirit of theatrical mischief. Gene Kelly's charm mirrors Hayley Mills's infectious screen presence, and it's constructed to make you smile.
But It's a musical, and if song-and-dance numbers feel dated or indulgent to you, nothing here will convince you otherwise.
Yours, Mine and Ours1968
Similar era, similar warmth, similar ensemble chaos. Lucille Ball brings the same controlled comic chaos that Rosalind Russell does, and the film finds genuine sentiment beneath the slapstick without sacrificing fun.
But The blended-family premise feels more sitcom than cinema now, and the pacing can feel slack by modern standards.
The Parent Trap1961
Another Hayley Mills vehicle about clever kids outwitting adults. It has the same gentle humor, the same affection for its characters, and proves Mills was genuinely one of the best young actors of the era.
But If you're tired of the "twins/doubles" plot device, this won't reinvent it for you.
Not sure tonight? Get a pick in a minute, starting from The Trouble with Angels
The wildcard
Something you would not have found on your own.
Morgan: A Suitable Case for Treatment1966
Both films explore the tension between youthful anarchy and the world demanding conformity, but Morgan argues that growing up is the real tragedy.
Released the exact same year as Angels, this is a British comedy about an eccentric artist whose childlike mischief and chaos upends everyone around him. Same era, same spirit of anarchic fun meeting authority, but seen from the perspective of someone who never grows up.
But It's much weirder and more avant-garde than Angels, with experimental filmmaking that can feel self-consciously clever. The protagonist is also genuinely exhausting.
More like this (8)
Please Don't Eat the Daisies1960
Doris Day leads an ensemble family comedy with the same relaxed warmth and genuine affection for its characters. It finds humor in observation rather than malice, which is exactly what Angels does so well.
But The family-comedy formula is predictable, and some of the gender politics have aged awkwardly.
Gidget1959
Sandra Dee as a spirited young woman discovering the world on her own terms. Lightweight but genuinely charming, with that same sixties optimism and a real understanding of teenage restlessness beneath the surface fun.
But The surfing setting dates it heavily, and the romance plot resolves in ways that feel very much of its time.
The Americanization of Emily1964
James Garner and Julie Andrews in a comedy that's smarter than it appears. It shares Angels' ability to ground humor in character and real emotion, finding depth without losing its lightness.
But It's a wartime romance, so the tonal shifts from comedy to something more serious might feel disjointed.
The Sound of Music1965
Another story about spirited young people and an authority figure finding unexpected common ground. Julie Andrews against Christopher Plummer, nuns, mountains, and genuine emotion beneath the musical numbers.
But It's a mega-musical, three hours long, and if the sentimentality overwhelms you, there's no escape from it.
Barefoot in the Park1967
Jane Fonda and Robert Redford bring effortless charm to a comedy about youthful energy bumping against older expectations. Quick, witty, and genuinely affectionate toward both generations.
But It's a two-hander romantic comedy, not an ensemble piece, and the New York apartment setting feels very confined.
The Graduate1967
Dustin Hoffman's anxious energy and the film's genuine sympathy for his confusion captures something real about the gap between generations and what adults actually see in the young.
But It's darker and more satirical than Angels, and if you're looking for warmth, this will feel ice-cold by comparison.
The Prime of Miss Jean Brodie1969
The mirror image of Angels: where that film asks if rebellious girls can understand their teachers, this asks if a beloved teacher can truly see and respect her students.
A boarding school story told entirely from the teacher's perspective, where Maggie Smith's charismatic educator is the chaos agent rather than the target. It has the same institutional setting and the same question about whether authority figures truly see the young, but inverted and much darker.
But It's a tragedy dressed as a drama, and Miss Brodie is seductive in ways that make the ending genuinely upsetting rather than redemptive.
Paper Lion1968
Both films find their warmth in the moment when one person truly sees another for the first time, and both trust that seeing to be enough.
A documentary-hybrid about a writer embedding himself with a professional football team, discovering that competence and vulnerability are often strangers. It shares Angels' genuine affection for people who seem uncomplicated but contain surprising depth.
But It's not a narrative film, and football culture means nothing if you don't care about the sport. Pacing is deliberate rather than brisk.
People
Cast
Hayley MillsMary Clancy
June HardingRachel Devery
Rosalind RussellMother Superior
Binnie BarnesSister Celestine- Camilla SparvSister Constance
Mary WickesSister Clarissa
Marge RedmondSister Liguori
Dolores SuttonSister Rose Marie
Margalo GillmoreSister Barbara
Portia NelsonSister Elizabeth
Marjorie EatonSister Ursula- Barbara Bell WrightSister Margaret
Directing
- Ida LupinoDirector
Writing
- Jane TraheyNovel
- Blanche HanalisScreenplay
Production
- William FryeProducer
Recommended by
Going My Way, Sister Act 2: Back in the Habit, Aiyyaa, Nasty Habits, The World of Henry Orient, 7 Khoon Maaf