The Best Summer Movies for Every Kind of Film Fan

By Marianne Paluso

Summer is a time for many fun-filled activities, from sunny vacations to trips to the beach, barbecues, picnics, and seeing the latest blockbuster at the movie theater. So if you’re a movie fan and want to indulge this summer in some older films that remind you of a bygone era, give you a sense of adventure or romance, and all in all feel like the perfect companion to that summertime bliss, this is the list for you.

Classic Films:

Gidget (1959)

Is there a more quintessential classic summer film than the misadventures of the girl they call “Gidget” and her surfing buddies “Moondoggie” and the “Big Kahuna” during one very wild and memorable summer? Starring Sandra Dee, James Darren (who also sings the title song), and Cliff Robertson, the story follows young Francie Lawrence, who is more interested in learning to surf than boys, until she completely flips for one of her fellow surfing enthusiasts.

Capitalizing on the surfing lifestyle craze of the “Endless Summer” era, this is early 60s old-fashioned fun but also surprisingly poignant in the innocent but sensitive looks at love, sex, broken hearts, and learning to find your place in the world. If you are looking for a classic beach film that is both light-hearted and thoughtful, Gidget is the one for you.

On An Island With You (1948) and Easy to Love (1953)

One could easily say you can watch any film starring “America’s Mermaid” of the 1950s in the summer, imagining yourself cooled off by the water sequences we see performed. And in truth, all of her films are colorful musicals with often silly but sweet and simple romantic plots.

But unlike other MGM musicals of the time, these films had one unique distinction that no other films did. They had Williams herself, a champion swimmer skilled at water ballet and synchronized swimming, so each of her movies had lovely, sometimes elaborate aquatic sequences that were incredible technical achievements but also absolutely delightful to watch.

There was only one Esther Williams. And these two films captured that summertime feeling so beautifully. In On An Island With You, Williams is a movie star making a film in Hawaii. It co-stars Ricardo Montalban as her leading man in life and the movie she’s making, Peter Lawford as the Navy Lieutenant hired as a technical consultant, and the man who’d been pining for her since they met years before.

This film also stars the wonderfully droll Jimmy Durante, talented Xavier Cugat, and beautiful Cyd Charisse, who shares some exquisite and sexy dances with Montalban. With a tropical paradise as a lovely setting and sweet and funny romantic entanglements that are happily resolved, On An Island With You is a frothy treat.

In Easy To Love, Esther trades in Hawaii for beautiful Cypress Gardens, Florida, as the overworked aquatic performer who does everything from pose for pictures with tourists to star in a spectacular water skiing show. She complains to her boss Ray (Van Johnson) daily but, in truth, hopes he will one day realize that he loves her as much as she loves him.

Of course, he may lose that chance when she’s fed up with her crazy schedule and his lack of appreciation and turns the head of a suave nightclub singer (Tony Martin) that she meets on a trip to New York.

Everything turns out the way you expect, but the actors are charming, the songs adorable, and the water skiing aquatic finale an absolute enthralling accomplishment in the combination of entertainment and athleticism. Overall, Easy to Love is a sunny, blithe, sun-kissed summertime joy.

Roman Holiday (1953)

In Audrey Hepburn’s first starring role, for which she won the Best Actress Academy Award, she stars as Princess Ann, who has embarked on a goodwill tour throughout Europe. During her stop in Rome, she runs away from her royal duties, frustrated and overwhelmed with every moment of her life decided for her.

She meets a handsome and kind reporter (Gregory Peck) who doesn’t let on that he knows who she truly is and offers to show her a wonderful time, so she can have a proper “Roman Holiday” and do whatever she wants the whole day long.

This includes anything from the simple joys of a new haircut and delicious gelato to gallivanting on a Vespa and the story of the Mouth of Truth. And soon, love blossoms inevitably.

While this isn’t a traditional romantic comedy with the happy ending subverting expectations, this film has no shortage of charm and classic romance thanks to Hepburn and Peck’s affable performances and understated chemistry. Most of all, the lovely locales and adventures through Rome give us all the desire for our own Italian summer holiday.

To Catch a Thief (1955)

The master of suspense Alfred Hitchcock’s lightest and most romantic mystery, To Catch a Thief, stars Cary Grant as a former jewel thief desperate to prove his innocence after a string of robberies employ all of his trademarks, and Grace Kelly as the daughter of one of the next potential theft victims.

Although the mystery and suspense are much more subdued than in Hitchcock’s other films, with more emphasis on the developing, often subtly amusing relationship between Grant and Kelly, there is still plenty of intrigue and the unique style Hitchcock was known for. Grant is debonair as always, and Kelly is as effortlessly beautiful and stylish as she ever was, while the stunning setting of the French Riviera provides a gorgeous backdrop for the story.

If you have ever dreamt of a summer in France complete with swimming, tours of classic gardens and castles, kisses amongst fireworks, and uncovering the person behind a notorious jewel heist, To Catch A Thief is for you.

Some Like It Hot (1959)

One of the greatest comedies of all time, from writer/director Billy Wilder, is also one of the best films to enjoy during the summertime. After witnessing a mob hit during the St. Valentine’s Day massacre in Chicago, two musicians (Tony Curtis and Jack Lemmon) flee for their lives, escaping notice by disguising themselves as women and joining an all-female jazz band.

Hilarity unsurprisingly ensues as Curtis’ Joe falls for ukulele player Sugar (a luminous Marilyn Monroe) and takes on yet another persona of a Shell Oil tycoon who owns a yacht and talks like Cary Grant. Meanwhile, Lemmon’s Jerry tries to stop the advances of an older and extremely wealthy gentleman to hilarious results.

A master class in comedy, Wilder brilliantly blends the intelligent and witty with the wacky and outlandish, with a good deal of romance thrown in for good measure as keeping their identities a secret grows more and more difficult. Filmed at the gorgeous Hotel Del Coronado in San Diego, California, Some Like It Hot is a silly and often sexy summer treat.

The Music Man (1962)

A slice of turn of the century Americana as sweet as apple pie, Meredith Wilson’s award-winning Broadway musical was brought to screen in fantastic fashion, with Robert Preston reprising his role as Professor Harold Hill, the likable confidence man who could charm the birds from the trees.

When Harold stops in River City, Iowa attempting his “forming a marching band con,” he is met with a challenge from the stubborn townsfolk, none more so than the kind but cautious librarian, Marian (Shirley Jones). Soon, however, he charms his way into their hearts, even the not easily charmed librarian when her shy, insecure younger brother (Ron Howard) is finally able to find something to be excited about.

But soon, his past catches up with him, and he discovers the biggest con he was pulling was on himself. The Music Man is filled with lively and colorful musical sequences, many of the songs familiar to anyone who has ever stepped foot on Main Street in a Disney Park, as well as sumptuous costumes of gauzy gowns, corsets, seersucker suits, and straw hats, as well as beautiful production design. This summertime musical is funny, sweet, and a true old-fashioned gem.

Family Films:

Pollyanna (1960)

Speaking of turn of the century Americana, this heartfelt and wholesome film turns the saccharine children’s novel into an introspective, believable and uplifting movie.

Featuring an impressive cast list of Hollywood veterans, including Jane Wyman, Agnes Moorhead, Adolph Menjou, Karl Malden, as well as Hayley Mills in his first starring role and first film for Walt Disney Pictures, Pollyanna tells the story of a young orphan who is sent to live with her wealthy Aunt Polly Harrington in the town named after her family.

In Harrington, Polly’s influence and affluence are everywhere, even in the Sunday sermons, which are frightening instead of uplifting. When Pollyanna comes into their lives, her positivity and ability to look on the bright side of things with her “Glad Game” soon change the hearts and minds of a town that had grown complacent and bitter. She teaches them to smile, believe in each other, and hope again, something they return to her when she needs it the most.

This inspiring film is simple but profound with gentle humor, beautiful production value, and exceptional and natural performances, especially from Mills herself. It is also a glorious summer companion with sunny adventures, especially a dazzling town bazaar with games, dancing, delicious watermelon, large, divine-looking cakes, and the singing of “America the Beautiful.” Pollyanna is the type of film you can feel Walt Disney in with every single frame, making it a true treasure.

Summer Magic (1963)

Another Disney film with a turn-of-century depiction of a bygone era starring Hayley Mills is this little film that may not be as well known as other films from the time but is equally worthy of viewing. One of the most apropos films to watch during the summer, the story follows the Carey family who has fallen on times of near destitution after the death of their father.

Learning to find happiness again, eldest Nancy inquires about the beautiful Yellow House she remembers seeing as a child on a family trip to the small town of Beulah, Maine. Soon the family moves in, and what follows are sweet misadventures, laughs, and heartfelt moments of optimistic Nancy, middle child musician Gilbert, youngest boy Peter who adopts a great big sheepdog, and their pretentious cousin Julia who comes to stay with them.

Moreover, we are treated to the presence of the wonderful Burl Ives as the big-hearted local general store owner Ossiam Popham, who humorously has let the Careys move in without the far away owner of the Yellow House’s permission.

The Sherman Brothers wrote endearing songs and a true vignette look at old-fashioned small-town life, Summer Magic, which takes place from early summer until Halloween, makes us long for days of balmy evenings, garden parties, and croquet, lingering on the front porch with a slow song and a sweetheart, and barnyard dances with pumpkins for decorations. This film has its own special kind of summer magic.

Coming of Age Films:

Stand By Me (1986)

A truly poignant and touching film, this film follows four teenage boys who embark on a journey to find the body of a local boy who went missing and is believed to have been tragically killed, most likely by a train accident.

The four friends, who feel like misfits and come from homes where their parents range from violent to distant and unloving, discover the true value of friendship, bravery, determination, and staying true to oneself along the way. Although this is a more serious film, the look at the summer days of the 1950s is rich and filled with moments of humor, while its wonderfully performed by its four young co-stars River Phoenix, Will Wheaton, Jerry O’Connell, and Corey Feldman.

Directed by Rob Reiner and featuring an incredible soundtrack of 50s classics, including the title song, Stand By Me is for anyone who remembers what it’s like to have a summer and genuine friendships that will stay with you forever.

Now and Then (1995)

Lauded as the teenage girl version of Stand By Me, and rightly so, Now and Then is just as wonderful and features equally poignant moments for the four young women who are dealing with the joys and pangs of growing up, and dealing with parents who have died, are getting divorced, or completely neglect them.

Also, similar to Stand By Me, the girls decide to find out the truth about the murder of a young boy and his mother, a tragedy that shook the small town many years before. But it should be noted that there are just as many hilarious and fun-filled moments for all the serious, tear-inducing moments.

Told in flashback form, we see the girls as adults and come together for the soon-to-be birth of a baby. Another film that features a rich look at a specific time period, this time highlighting the 1970s, and an exceptional soundtrack, Now and Then, is both touching and light summer fare for the young and young at heart.

 The Sandlot (1993)

If you are a fan of this film, chances are you have said the line “You’re killing me Smalls” while indulging in the tasty summertime treat of smores. But whether you have seen this film for the hundredth time or have yet to see it, The Sandlot is another worthy one in the array of summer movie companions.

Following a group of young boys who spend their summer days playing baseball and learning about themselves along the way, they get into the “biggest pickle of their lives” when the awkward newbie Smalls unknowingly uses a baseball signed by the legendary Babe Ruth for their game.

The ball is hit into the backyard next door by their best player Bennie, and they are too scared to retrieve it because of the large dog residing there they call “the Beast.” In another distinct time period, this time the 1960s, this coming-of-age tale is hilarious, heartfelt, and for those who play or can appreciate America’s pastime.

It’s also a foregone conclusion that anyone who watches this film will try to replicate the moment when the fireworks dazzle them all, and “America, the Beautiful” by Ray Charles, plays in the background. Sweet summertime fun, The Sandlot most definitely is.

The Sisterhood of the Traveling Pants Films (2005, 2008)

Over the course of two summers where best friends Tibby, Carmen, Lena, and Bridget part and come back together again, these four very different young women experience the trials and tribulations and growing up during the transition from childhood to adulthood, dealing with loss, love, broken hearts, family issues, and finding where they fit in this world, all while remaining true to not only the women they are becoming, and still clinging to the friendship they hold so dear.

After finding a pair of jeans that miraculously fits them all, despite them all being very different shapes and sizes, they decide to share them and send them to each other during their summers apart. Lovely and artistic Lena (Alesis Bledel) travels to sun-kissed blissful Santorini, Greece. She unexpectedly finds love and then must see if that love is forever or simply heartbreak as she expands her artistry at summer school.

Tibby (Amber Tamblyn) discovers the preciousness of life while trying to make a documentary and befriends a young girl with cancer, then deals with relationship woes and the fear of truly loving someone. Carmen (America Ferrera) must learn to open up to her father, who has found himself another family, then to stand up for herself when attending a dramatic summer school.

And Bridget (Blake Lively) learns to deal with the loss of her mother, with the painful realization of rushing into a physical relationship, then reconnecting with a long-lost grandmother. Each story is thoughtful and well performed on its own, but together we see an unbreakable bond as soft and supportive as a well-worn pair of jeans.

Adventure Films:

Pirates of the Caribbean: The Curse of the Black Pearl (2003)

The first and greatest installment in the wildly successful franchise harkens back to old-fashioned swashbuckling adventures of the past with traditional character and story beats, including a pirate siege of a town, a kidnapped girl, and the dashing hero who vows to rescue her, with the characters of Elizabeth Swann (Keira Knightley) and Will Turner (Orlando Bloom).

But then the film gives us both a classic and more modern adventure, subverting our expectations. There is a supernatural twist involving cursed pirates and a not-so-damsel in distress with Elizabeth, who, though kidnapped and scared, is also brave, forceful, tough, and enamored with the excitement of piracy.

Will is the traditional hero but still willing to do what is right no matter the cost. And most significantly, there’s the character of Captain Jack Sparrow, brought to life in a way only Johnny Depp could have done, making Jack equally clever and cunning, hilarious and off beat. You never know where his allegiances lie, making him endlessly fascinating, especially with his repartee with other characters, including the villainous Barbossa (Geoffrey Rush).

The adventures and twists in this film, the performances, characters, stunning locations of the Caribbean, incredible special effects, and rousing score make Pirates of the Caribbean the perfect fun-filled but captivating summer adventure flick.

Independence Day (1996)

A perfect adventure film, this alien invasion chiller takes place in the heat of summer on the fourth of July, America’s Independence Day, a day in the movie that becomes the day the world proclaims and wins its independence from these galactic invaders.

Following various characters, including the President of the United States (Bill Pullman), a cocky but gifted Marine fighter Pilot (Will Smith), and a brilliant satellite engineer (Jeff Goldblum), the setup for the story may be fantastical, and the film itself may be that kind of cheesy popcorn flick, but sometimes what we need is popcorn- something tasty that leaves us feeling good and satisfied.

Moreover, the frights and the feelings are legitimate as we can put ourselves in the minds of a world that is invaded with no warning or motif, which is extremely scary, and characters who are fighting for those they love, themes that are as timeless as can be. Independence Day is often uplifting and always a thrilling ride from start to finish.

Thriller/Horror:

Jaws (1975)

Truly the first film of its kind that embodies what has become known as the “summer blockbuster,” Steven Spielberg’s film is for those looking for a thrill, and a fright, along with a strong story and character beats, in their summer movies. And Jaws is one of the greatest ever.

Masterful in terms of dramatic tension, with the use of the now-iconic score by John Williams, Spielberg gives us a tale of the peaceful beach town of Amity, in Long Island, New York, suddenly plagued by killer shark attacks.

The story follows Sherriff Martin Brody (Roy Scheider) as he attempts to handle the situation and keep residents and visitors safe, clashing with the foolish Mayor, who is more concerned with money and tourism, and then teaming up with a marine biologist (Richard Dreyfuss) to hunt down this shark, and stop the vicious attacks once and for all.

There is no doubt why this film is as quotable and iconic as it is, but Jaws also features small moments of great depth that are often overlooked. Although the attacks may not be true to life, the feeling of authenticity never waivers, making Jaws both an exciting and grounded summer thriller.

I Know What You Did Last Summer (1997)

For those looking for a true horror film for the summer, look no further than the first and best of this franchise that offers a great deal of the types of chills and thrills you expect from a teen slasher film.

Following a group of friends, Julie, Helen, Ray, and Barry, on the eve of their high school graduation, a tragic accident occurs when they accidentally hit and killed a man while driving too fast on a winding road. The four foolishly dump the body in the ocean, vowing to never speak of the incident again.

But a year later, after they all tried to pretend that night never happened, Julie receives a note saying “I know what you did last summer” and returns home to find her friends have not been the same since. Soon the man seemingly returns from the grave and begins terrorizing them all, and the results are chilling.

Featuring an excellent cast including Jennifer Love Hewitt, Sarah Michelle Gellar, Freddie Prinze Jr., and Ryan Phillipe, this summer set film shows us dangers lurking behind the fun festivities, and it’s absolutely, terrifically terrifying.

Romance Films:

Elizabethtown (2005)

A truly beautiful look at life, love, death, friendship, and family, this film from Cameron Crowe features his distinct storytelling style and a great deal of heart, tears, and laughs. After he causes a major fiasco that loses his company nearly a billion dollars, Drew Baylor comes close to ending it all.

But at that moment, he gets a call that his father has passed away when visiting his brother in the small town of Elizabethtown, Kentucky. Drew is then tasked to go there, bring his father home, and deal with the part of the family that they have never been close with.

And Drew is met with an unexpected outpouring of affection from an array of family members and friends, showcasing that age-old southern hospitality and humor you can find in these little towns, with just a bit of stubbornness and misunderstanding.

The stress of everything Drew is going through finds a ray of sunshine in the flight attendant he meets and then befriends during an all-night phone call that changes their lives forever. Claire is the effervescent and cheerful woman Drew needed, and he is the deep down, sweet and understanding man she needed.

This optimistic woman has her own insecurities and pangs of sadness as she feels like “The substitute person.” As the families come together to honor the fallen, Claire and Drew grow closer as she plans a road trip home for him. And we see in these moments that truly miraculous things are everywhere and found in even the smallest people and places, if we only learn to look past our failures and lean into love.

And all in all, Elizabethtown is filled with that beautiful Crowe style of dialogue, characterizations, incredible soundtrack and mandolin, and folksy score from his wife Nancy Wilson, creating a profound summertime romance.

50 First Dates (2004)

Adam Sandler and Drew Barrymore have made three romantic comedies together, and none are more moving and sweetly funny than this perfect-for-summer, Hawaiian-based tale. When Henry meets Lucy at a restaurant one day, he is instantly smitten with her, and she with him, giving Henry the hope that he has finally found his dream girl.

But when he sees her again the next day, she has no memory of meeting him, and he finds out that Lucy suffers from short-term memory loss after getting into a horrible car accident years before. With the help of her caring father and brother and the compassionate locals, they shield Lucy from the truth as she keeps reliving the same day, every single day.

Instead of running from this impediment, Henry decides he wants to try to make Lucy fall in love with him every day, making this a unique and surprisingly touching film. Featuring Sandler’s typical brand of comedy, what makes 50 First Dates stand out are the deeply moving moments of steadfast devotion and commitment and the stunning Hawaiian locations, making this a breezy summer rom-com to lift the spirits.

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This post was previously published on Wealth of Geeks.

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