All 24 Ashley O’Leary Movies In Order — All The Best (And Worst) Films To Watch Online

Dennis Hernandez
10 min readMay 22, 2024
Ashley O'Leary Movies

Get ready to dive into the world of mesmerizing cinema with our roundup article on Ashley O’Leary movies! This talented actress has graced the big screen with her remarkable performances, captivating audiences with her on-screen presence. Join us as we explore her impressive filmography, highlighting her most memorable roles and discussing what makes each movie a must-watch.

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1. Double, Double Toil and Trouble (1993)

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In the whimsical and magical world of “Double, Double Toil and Trouble” (1993), two adorable little girls, Hallie and Anabel, team up to save their parents from their evil Aunt Agatha on Halloween night. Full of surprises, these precocious youngsters meet mysterious friends and venture on a journey filled with magic, witches, and adventure.

👉 View free on Amazon Prime

2. How the West Was Fun (1994)

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“Westward Bound with Fun” is a charming, 1994 comedy movie featuring Mary-Kate and Ashley Olsen as two resolute sisters vying to safeguard their beloved ranch from shrewd adversaries. Filled with slapstick wit and buddy comedy antics, this modern-day western captivates audiences of all ages with whitewater rafting escapades and thrilling plot turns.

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3. The Little Rascals (1994)

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The Little Rascals is a heartwarming and nostalgic family comedy film that has been a fan favorite since its release in 1994. Set in the 1930s, the movie follows the loveable misadventures of a group of children, led by the charming Alfalfa, as they attempt to win the heart of their dream girl, Darla. The boys’ plan to pull off the biggest prank of their lives goes hilariously awry, leading to a series of comical predicaments and adventures.

👉 Stream for free at Amazon Prime

4. It Takes Two (1995)

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“It Takes Two, “ released in 1995, is a heartwarming comedy about two unrelated girls, Alyssa and Amanda, who are identical strangers. Their lives take an unexpected turn when they accidentally meet, leading to a series of hilarious mishaps and identity swapping. As they navigate through these embarrassing situations, the girls discover the power of friendship and learn to embrace their differences.

👀 Watch for free with Amazon

5. Billboard Dad (1998)

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In the heartwarming family comedy “Billboard Dad, “ two spirited and sassy sisters take it upon themselves to find the perfect love interest for their newly single father. When their beach-loving dad decides to move back to the city, the twins embark on a hilarious cross-country adventure, transforming their father and his life in the process.

👉 View for free on Amazon Prime

6. Passport to Paris (1999)

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Discover the magical adventure of the Olsen twins, as they find themselves in beautiful Paris in “Passport to Paris. “ Sent to visit their grandfather, Ally and Mel stumble upon a whirlwind of love and excitement. Exploring the charming city, the twins befriend two charming French boys and immerse themselves in the French way of life.

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7. You’re Invited to Mary-Kate & Ashley’s Greatest Parties (2000)

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Get ready to party with Mary-Kate and Ashley in their energetic musical adventure, “You’re Invited to Mary-Kate & Ashley’s Greatest Parties”! Released in 2000, this fun-filled movie brings the twin sisters to the forefront, showcasing their lively dancing and singing skills. With a runtime of 1 hour and 30 minutes, this film invites you to join in the excitement as Mary-Kate and Ashley throw the most unforgettable parties ever, complete with catchy tunes and irresistible choreography.

View now free via Amazon Prime

8. Our Lips Are Sealed (2000)

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“Our Lips Are Sealed” is a family-friendly comedy film that brings together the Olsen twins in a unique setting. In the movie, the Parker sisters are relocated by the FBI after stopping a diamond thief by using ketchup. Their new home is in Sydney, Australia, where they find themselves in the midst of chaos and hilarious situations.

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9. Holiday in the Sun (2001)

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Bursting with sun-soaked fun and family-friendly humor, Holiday in the Sun follows the extraordinary adventures of twins Madison and Alex. Taken on a winter break to the enchanting Bahamas, the sisters quickly find themselves entangled in a thrilling quest to uncover the truth about a mysterious man who is smuggling stolen artifacts. As they navigate their way through exotic locales, exotic creatures, and colorful characters, the girls learn the importance of unity, trust, and loyalty while having the time of their lives.

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10. The Favorite Adventures of Mary-Kate and Ashley (2001)

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“Mary-Kate and Ashley: Their Top-Notch Adventures” is an enchanting compilation film, merging the Olsen Twins’ most cherished direct-to-video escapades. In this heartwarming family-oriented film, viewers will experience the Olsen Twins in their iconic roles, as they dive into exhilarating quests, unravel mysteries, and share countless captivating moments. With a runtime of 1 hour and 30 minutes, this nostalgic trip will transport viewers through time, as the twins tackle various obstacles while celebrating their strong bond.

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11. Winning London (2001)

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“Winning London” is a delightfully adventurous family comedy film, released in 2001. The story revolves around high school sweethearts, Chloe and Riley Lawrence, who receive an invitation for a once-in-a-lifetime opportunity to join the International Model UN competition in London. While their minds are focused on representing their state in negotiations and diplomacy, their hearts are set on exploring the stunning sights and finding love in the land of British charm.

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12. When in Rome (2002)

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When in Rome is a delightful family comedy featuring twin sisters, Heidi and Charli, as they embark on their first internships at a prestigious international fashion company in Rome. Despite facing some initial challenges, they eventually find their footing and catch the eye of the company’s owner’s charming nephew, as well as a charming Roman man. As they navigate through the exciting world of fashion and forge new friendships, will they find the romance they are looking for?

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13. Getting There (2002)

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Getting There is an adorable comedy film that stars the twins, Mary-Kate Olsen and Ashley Olsen, who just turn 16 and are excited to get their driving licenses. The film follows their journey as they set off on a road trip with two friends to the Winter Olympics in Utah. Their male friends decide to join them in their own car, and all the fun adventures begin.

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14. 2002 MTV Video Music Awards (2002)

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Get ready for an unforgettable night of music and entertainment as you witness the 2002 MTV Video Music Awards! Hosted by the hilarious Jimmy Fallon, this star-studded event celebrates the 19th annual awards ceremony. Prepare to be amazed by iconic performances from legendary artists, including Bruce Springsteen and the E Street Band, Pink, Ja Rule, Ashanti, and Nas, Shakira, and Eminem.

📽️ Watch now for free on Prime

15. Charlie’s Angels: Full Throttle (2003)

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“Charlie’s Angels: Full Throttle” (2003) is an exhilarating action-adventure comedy film that stars Drew Barrymore, Lucy Liu, and Cameron Diaz as the infamous Charlie’s Angels. As the Angels dive into a high-risk operation, they soon find themselves entangled in a web of crime, danger, and unexpected thrills.

📽️ Watch now free at Amazon Prime

16. The Challenge (2003)

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“The Challenge” follows the story of estranged teenage sisters, Kelly and Lizzie, who find themselves thrust into a wildly unexpected adventure as teammates on the TV show “The Challenge, “ a thrilling Survivor-style competition in picturesque Cabo San Lucas, Mexico. The reunion of these opposites is just the beginning of a comedic, action-packed journey overflowing with surprise twists and turns. As they embark on a series of challenges designed to test their strength, endurance, and sisterly bond, the twins navigate their way through the unknown together.

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17. Last Laugh ’04 (2004)

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Last Laugh ’04, released in 2004, is a stand-up comedy showcase filled with hilarious routines by some of the biggest names in the world of comedy. This one-hour, thirty-minute film takes you on a rollercoaster ride of laughter as you witness these comedy giants showcasing their skills, taking on topics ranging from everyday life to the absurd. With an impressive roster of A-list stars like Ben Affleck, Yasser Arafat, and Lance Armstrong, the film promises to deliver an unforgettable New Year’s Eve celebration as it brings together the best of sketch and stand-up comedy.

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18. New York Minute (2004)

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New York Minute is a heart-warming family adventure in which two rebellious sisters, Jane and Roxy, find themselves on a memorable journey through New York City. After their mother’s death, Jane focuses on her studies as a good student, while Roxy is more carefree and rebellious.

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19. The Child Star Jinx (2005)

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The Child Star Jinx (2005) explores the world of child stardom and the trials it brings with a unique and in-depth look at the lives of former high-profile child actors. Set against the backdrop of the UK film industry, this documentary delves into the successes and downfalls faced by young stars as they navigate through their careers.

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20. Factory Girl (2006)

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“Factory Girl” is a biographical drama that captures the tumultuous life of socialite Edie Sedgwick as she navigates through her relationships with Andy Warhol and a folk singer. Sienna Miller, Guy Pearce, and Hayden Christensen lead the star-studded cast, while directors George Hickenlooper and Aaron Richard Golub bring their unique vision to the film.

➡️ Watch free at Amazon

21. Saturday Night Live: The Best of Commercial Parodies (2006)

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Laugh the night away with Saturday Night Live: The Best of Commercial Parodies! This hilarious TV special, hosted by the ever-charismatic Will Ferrell, is a treasure trove of some of the most hilarious commercial parodies ever seen on TV. Hand-selected from the show’s first 31 seasons, prepare to be in stitches as you witness iconic comedians like Ben Affleck and Fred Armisen go toe-to-toe in their quest for comedic glory.

👉 Watch free at Amazon Prime

22. The Wackness (2008)

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The Wackness is a heartwarming coming-of-age comedy-drama set in the summer of 1994, in the pulsing heart of New York City. As hip-hop culture permeates the city, we follow the story of lonely teenager Luke Shapiro, who finds an unconventional way to make his last summer before university memorable. His unique business model revolves around selling marijuana throughout the city while trading it with his unorthodox psychotherapist for treatment, all while harboring a crush on his stepdaughter.

👉 Watch free on Amazon Prime

23. Beastly (2011)

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“Beastly” is a modern-day retelling of the classic fairy tale “Beauty and the Beast. “ Set in bustling New York, teenaged Kyle Kingson, skillfully portrayed by Alex Pettyfer, finds himself transformed into a hideous monster after an act of retribution. Left with just his beauty-enhanced laptop and his disfigured body, Kyle must now embark on an extraordinary journey to find true love.

➡️ Stream now free at Amazon

24. Scatter My Ashes at Bergdorf’s (2013)

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“Scatter My Ashes at Bergdorf’s” is an enthralling documentary that takes viewers on a mesmerizing tour through the legendary Manhattan department store, Bergdorf’s. Directed by the talented Matthew Miele, this film boasts a captivating lineup of interviews with an eclectic range of fashion designers, style icons, and celebrities. These noteworthy personalities generously share their insights and experiences surrounding the iconic retailer, shedding light on the captivating realm of high-end fashion.

➡️ View for free on Amazon

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