Film

The Lemon Drop Kid

Name: The Lemon Drop Kid
Genre: Comedy, Crime
Released: 1951
Cast: Bob Hope, Marilyn Maxwell, Lloyd Nolan, Jane Darwell, Andrea King

Comedy
Con-artist caper
Light-hearted

A Bob Hope comedy about a con artist who accidentally stiffs the wrong gangster and invents a fake charity scam to pay him back by Christmas. It's silly, fast-paced, and built on the pleasure of watching criminals outwit each other while dressed as Santas. Perfect if you love old Hollywood wisecracks and don't mind plot holes the size of Manhattan.

TMDb rating

3.3

If you liked this

It's a Wonderful Life1946

A masterpiece about redemption and community that also uses Christmas as its frame. Where Lemon Drop Kid uses the season for chaos, this channels it toward genuine grace—but both films trust that ordinary people are worth saving.

But It's been shown to death and quoted endlessly. The emotional weight can feel heavy if you want something lighter.

His Girl Friday1940

Screwball comedy at full throttle, with dialogue that ricochets like machine-gun fire. Cary Grant and Rosalind Russell play people trying to outsmart each other, and the rhythm is intoxicating. Same era, same energy.

But The pacing is relentless and the plot barely matters. If you like character development or quiet moments, you'll feel whiplashed.

Some Like It Hot1959

The greatest comedy ever made, full stop. Men disguised as women, gangsters chasing them, a roaring band, and actual warmth underneath the chaos. Tony Curtis and Jack Lemmon nail every beat that Hope reaches for here.

But It's a classic that's been praised forever, which can breed resistance. Also, the gender comedy rests on assumptions that read differently now.

Not sure tonight? Get a pick in a minute, starting from The Lemon Drop Kid

The wildcard

Something you would not have found on your own.

Scrooge1951

Both use Christmas as the deadline for moral reckoning; both ask whether someone incapable of genuine feeling can be saved.

Released the same year as Lemon Drop Kid, this is Scrooge McDuck's origin story—but Alastair Sim's performance is so human and strange that it transcends Disney. A con man redeemed by ghosts instead of a fake charity; both films use Christmas to ask what people owe each other.

But It's slow and deliberately paced where the Kid darts around. Also, the Donald Duck framing device is dated, even if Sim's performance has aged perfectly.

The Sting1973

A con-man film that loves its own ingenuity and treats a massive scam as an art form. Paul Newman and Robert Redford are charming crooks, and the pleasure is purely in watching the scheme unfold. No moral weight, just satisfaction.

But The plot is the whole thing. If you need character depth or thematic resonance, there's not much here.

Ocean's Eleven1960

The original Rat Pack heist film: slick, witty, and deeply in love with its own coolness. Frank Sinatra and his crew steal a casino for fun, and the film never pretends it's about anything but style and camaraderie.

But The plot has holes you could drive a truck through, and the women exist mainly to be won or impressed. It's a dated pleasure.

Guys and Dolls1955

A musical about gamblers and con artists in New York, with Marlon Brando and Frank Sinatra singing in the streets. It's got the same affection for lovable lowlifes that the Kid does, plus genuine swagger and style.

But The musical numbers can feel stagey and elongated if you're not in the mood. Brando's singing is... not technically trained.

The Philadelphia Story1940

Cary Grant, Katherine Hepburn, and James Stewart in a comedy about the rich and beautiful falling apart, then fixing themselves. Smart dialogue, perfect timing, real chemistry. A masterclass in making confusion charming.

But The class politics are deeply of their time. The film loves its wealthy characters in ways that can feel alienating now.

Singin' in the Rain1952

Pure joy in movie form. Gene Kelly, Donald O'Connor, and Debbie Reynolds in a Hollywood musical that's genuinely funny, beautifully made, and utterly unselfconscious about loving itself. The energy is irresistible.

But If musicals feel like dead time to you, this won't convert you. It's also relentlessly cheerful, which some find cloying.

Breakfast at Tiffany's1961

Audrey Hepburn as a New York con artist and dreamer, all style and evasion. It's lighter than it seems, funny in the margins, and gorgeously shot. Same DNA as the Kid—beautiful people doing dubious things.

But The racist caricature is impossible to overlook. Also, the romance feels thin if you're looking for genuine connection.

The Ladykillers1955

A gang of small-time crooks brought low by their underestimation of an old woman who represents community and kindness they can't fake.

Ealing Studios made a British answer to American caper comedies: five con men posing as musicians rent a room from an elderly landlady and slowly realize she's outwitting them. It's warmer and quieter than the Kid, but the formula—criminals undone by decency—is the same.

But British comedy rhythm feels slow to American ears sometimes. Also, some characters are drawn with ethnic caricature that hasn't aged well.

Sullivan's Travels1941

Both hinge on a lie about charity; both ask whether the joke is worth what it costs, and what kindness really means.

Preston Sturges' masterpiece about a wealthy director who pretends to be poor to understand suffering, then gets mistaken for a vagrant and arrested. It's funny and tragic at once, asking what comedy is for. A con built on the same lie the Kid sells: that you can fake charity.

But The tonal shift from comedy to genuine darkness will jar you. The second half doesn't land unless you're willing to follow it into actual sadness.