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Rosie O’Donnell’s movies are like O’Donnell herself — funny, smart, and full of heart. She has made a big impact in movies and TV. From comedies to serious stories, Rosie always brings something special. If you want to check out the best O’Donnell movies, this list is the perfect place to start. These five films show why fans love her so much.

1. ‘A League of Their Own’ (1992)

A League of Their Own is one of the most loved O’Donnell movies. She plays Doris Murphy, a tough and funny baseball player. The movie tells the story of an all-women baseball league during World War II. Rosie stands out with her great comic timing and strong acting. She works alongside big stars like Madonna, Tom Hanks, and Geena Davis. The film mixes laughs and heart, showing how women proved they could play just as well as men. Rosie’s role made her a movie star. Fans still quote her lines today. This film is a classic that everyone should watch at least once.

2. ‘Now and Then’ (1995)

In this touching O’Donnell movie, she plays the adult version of Christina Ricci’s character. The film tells the story of four girls who stay close friends over the years. Rosie plays Roberta, a tomboy who becomes a doctor. The movie shows flashbacks from childhood and how those memories shape the future. Rosie brings strength and kindness to her role. The story connects with anyone who values friendship. It’s a mix of fun and feelings. If you enjoy coming-of-age movies with heart, this one is a great pick. Rosie shines in this special film.

3. ‘Harriet the Spy’ (1996)

Rosie plays Golly, the cool and caring nanny in this fun O’Donnell movie. She supports Harriet, a young girl who dreams of becoming a writer. Golly helps Harriet deal with growing up, friendship troubles, and learning from mistakes. Rosie’s performance is warm and wise. She balances humor and heart in every scene. This movie is great for kids but also enjoyable for adults. Rosie and the young cast have great chemistry. If you like stories about being yourself and learning from life, you’ll love this one. Rosie makes Golly a character you’ll never forget.

4. ‘Sleepless in Seattle’ (1993)

Rosie plays Becky, Meg Ryan’s best friend, in this classic romantic comedy. This O’Donnell movie adds the perfect dose of humor to a sweet love story. Becky gives advice, listens to problems, and delivers funny one-liners. Rosie and Meg Ryan have great friendship chemistry. Her scenes might be short, but they leave a big impression. She brings laughs and warmth without stealing the spotlight. The movie is about love, destiny, and second chances. If you like romantic comedies, this is a must-watch. Rosie’s performance adds a lot of charm to the story.

5. ‘Riding the Bus with My Sister’ (2005)

This is one of the most powerful O’Donnell movies. She plays Beth, a woman with an intellectual disability who rides buses all day. The story follows Beth and her sister as they reconnect and grow closer. Rosie takes on a very serious role and gives it her all.

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Her performance shows care and deep emotion. It’s different from her usual funny parts. This film shows her range as an actress. If you want to see Rosie in a role full of feeling and truth, this movie is a great choice.