13 Movies to Watch When You’re Craving Nostalgia

Photos courtesy of Walt Disney Pictures, Warner Brothers, Dimension Films, and Miramax Films.

Why do we crave nostalgia? Maybe it’s to relive our childhood or get that fuzzy feeling in our cores? I can say that I adore nostalgic movies, specifically ones from my childhood. Today, I want to share the movies that take me back to my childhood with all of you. Let’s get started.

Here are 13 movies to watch when you’re craving nostalgia.

1. The Parent Trap (1998)

The Parent Trap is one of those films that never gets old for me. I’ve watched it so many times now so I don’t remember the first time I watched it. Lindsay Lohan’s breakout roles as twins Hallie and Annie are the sole reason why her career took off. Her comedic timing in this is spot on and it’s amazing how she was able to portray two characters that were so different from each other.

The late Natasha Richardson is stellar as Elizabeth James. I just adore her character in this so much. She added class and elegance to the character. I like the offsetting of Nick Parker (Dennis Quaid). They had great chemistry.

This film takes me back to my childhood every time I watch it because I watched it so much when I was a kid.

2. Harry Potter and the Sorcerer’s Stone (2001)

Harry Potter and the Sorcerer’s Stone is one of my top 3 favorite films from the Harry Potter film series. I’ve watched it so many times. It’s one of my comfort films because it provides so much comfort. It makes me feel like I’m home.

Daniel Radcliffe, Rupert Grint, and Emma Watson are all adorably charming and they’re so young in this. I fell in love with Ron and Hermione instantly. Ron was so awkward and adorable in this and Hermione doesn’t change really at all in the rest of films except that she just grows up. I know Harry is the main character but I’ve never been a huge fan of him. I loved him in this film but he got very self-involved in the rest of the franchise.

There’s something magical about this world that makes you feel like you’re getting the best hug ever.

3. The Princess Diaries (2001)

The Princess Diaries introduced me to one of my favorite fictional characters of all time. Mia Thermopolis (Anne Hathaway) is someone I related to as a kid but more so as a teenager.

This film is coming-of-age through and through because it focuses on Mia as she learns that she’s next in line for the Genovian throne. As she learns the ways of royalty, Mia discovers that she needs to grow up in order to rule an entire country.

I love the chemistry between Anne Hathaway and Julie Andrews in this so much. Julie Andrews is one of my favorite actresses. She’s so classy and incredibly talented. The original film is an essential viewing for those of you out there who are dealing with the trials and tribulations of growing up.

4. Spy Kids (2001)

Spy Kids is the film that started the Robert Rodriguez cinematic universe and spawned multiple sequels to this kooky and action-filled family adventure. I wouldn’t say that I’ve seen this film a lot but I’ve seen it enough to remember most of it. Every time I rewatch it, I notice something new or something that I completely forgot that happened.

It’s hard to believe that the film turned 20 years old in 2021. It’s harder for me to believe that Meghan Trainor is married to Juni Cortez (Daryl Sabara). I do love that the film is inclusive and has representation.

5. Spy Kids 2: The Island of Lost Dreams (2002)

Spy Kids 2: The Island of Lost Dreams is my favorite film out of the Spy Kids film franchise. It’s the film I watched the most when I was a kid. I don’t know why. I guess I found the story to be more engaging and entertaining than its predecessor.

Let’s not forget that Emily Osment portrays Gerti Giggles and goes on to star in Hannah Montana and Taylor Momsen who portrays the President’s daughter goes on to be in Gossip Girl. The cast is stacked for sure.

The film turned 20 years old last year which is crazy.

6. Freaky Friday (2003)

Freaky Friday is not only one of my favorite films from my childhood but one of my favorite films ever. Here’s Lindsay Lohan killing it as per usual. She brought Anna Coleman to life in the best way possible. Her chemistry with Jamie Lee Curtis and camaraderie was a plus.

I’d watch this film when I’d go on road trips to Walt Disney World when I was younger.

You can’t lie and say that Take Me Away isn’t one of the best cover songs from a film. Christina Vidal’s vocals are everything and the scene where they perform the song in the film is legendary.

Welcome to the multiverse where Cayden Boyd from The Adventures of Sharkboy and Lavagirl stars as Harry’s (Ryan Malgarini) friend. You know the scene where Harry is in Anna’s room trying on her bra? I’m laughing by just writing all this out.

Oh and the film turns 20 this year. My mind is blown.

Seriously, if you haven’t watched Freaky Friday yet, you’re missing out on one of the best films to exist in cinema history.

7. The Lizzie McGuire Movie (2003)

The Lizzie McGuire Movie is one of those films that escapes you from reality. I mean Lizzie (Hilary Duff) does go to Rome, Italy and meets a handsome popstar (Yani Gellman). What seems like fantasy turns into a nightmare eventually.

How can we not forget Miss Ungermeyer (Alex Borstein)? We can all agree that she was very annoying, right? I hope so. I can say that I wasn’t an avid watcher of the series but I love this film.

What’s hilarious to me is that Jake Thomas who portrays Lizzie’s little brother, Matt, is friends with YouTubers Aaron Burriss and Veronica Merrell. I remember watching one of Aaron’s vlogs and I saw him. I was like, “that’s the dude who played Matt in Lizzie McGuire.” I guess it’s a small world after all.

All there’s left to say is sing to me Paolo! Just kidding. You really don’t have to. Seriously. You don’t.

8. The Princess Diaries 2: Royal Engagement (2004)

The Princess Diaries 2: Royal Engagement is better than the original. I’m sorry but I’ve always loved the sequel more than the original. Don’t get me wrong, the original is iconic but I just love the second film so much.

I would watch it along with Freaky Friday on my road trips to Walt Disney World with my mom.

I absolutely love the chemistry between Anne Hathaway and Chris Pine. They invented the enemies to lovers trope in film. It’s a fact.

I love that the sequel is set in Genovia so it’s a fresh setting for audiences to experience. I love the scene where Mia is trying to pick out her next husband with Lilly (Heather Matarazzo), Charlotte (Kathleen Marshall), and Clarisse (Julie Andrews).

Let’s not forget that Raven-Symoné portrays Asana. Raven puts so much effort and energy into the characters she brings to life on screen.

I don’t want a third film if these two and Julie Andrews aren’t it. It also won’t be directed by Garry Marshall because he past away.

9. Ella Enchanted (2004)

Ella Enchanted is another film that was a huge part of my childhood. What a surprise. I feel like Anne Hathaway and Lindsay Lohan dominated the 2000s. The irony that this and The Princess Diaries 2 were released during the same year.

I love this film so much. I love the chemistry between Hathaway and Hugh Dancy. I can’t believe he’s a part of the Law and Order cinematic universe now and that’s he has an American accent. I love the fantasy aspect and the ensemble cast. Cary Elwes, Heidi Klum, Minnie Driver, and Vivica A. Fox? I mean, c’mon.

It’s cool that it’s almost a parody of Cinderella except the prince knows what the princess looks like and she didn’t lose her shoe but got thrown into jail instead.

10. The Chronicles of Narnia: The Lion, The Witch, and the Wardrobe (2005)

The Chronicles of Narnia: The Lion, The Witch and the Wardrobe is one of my favorite comfort films. I don’t know what is in this film but it feels like a soft and comfy blanket.

It’s an adaptation of the novel by C.S. Lewis. I can’t personally say that it hits the nail with the book since I never read it but I can say that the film itself is so good. I aspired so much to be like Susan (Anna Popplewell) and saw so much of myself in Lucy (Georgie Henley).

The first film spawned two sequels that feature Ben Barnes as Prince Caspian and Will Poulter as Eustace. Barnes has gone on to star in the Netflix series, Shadow and Bone, which is based on the books by Leigh Bardugo. Poulter will appear in the final installment of Marvel’s Guardians of the Galaxy as Adam Warlock.

11. The Adventures of Sharkboy and Lavagirl (2005)

The Adventures of Sharkboy and Lavagirl is a fever dream. That’s how I’d describe it to someone who asked me what the film is like. It’s from the mind of Robert Rodriguez who gave us the Spy Kids franchise.

Two Taylor’s in one film is like a multiverse in itself. Here we have a young Taylor Lautner. Who knew that he would go on to star in the Twilight films, one of the most popular film franchises to date.

Oh but wait. There’s also a young Sasha Pieterse who portrays Marissa and goes on to star as Alison DiLaurentis in Pretty Little Liars. George Lopez who portrays and voices a number of characters.

Like I said, this film is an acid trip.

12. Enchanted (2007)

Enchanted is an underrated Disney gem. I cannot tell you how Amy Adams kills her role as Giselle. She brings her to life so effortlessly. Julie Andrews narrates this masterpiece and puts her narrator skills to work for Netflix’s hit series, Bridgerton. James Marsden portrays the lovable himbo Prince Edward. Jodi Benson is Robert’s (Patrick Dempsey) co-worker and known for her iconic role as Ariel in The Little Mermaid.

I love that the film combines romance, fantasy, and musical elements. I’m not a huge musical fan but I love Disney musicals.

A sequel was released in 2022 and it didn’t have the same magic the original film had. It was a bit disappointing.

13. Hannah Montana: The Movie (2009)

Hannah Montana: The Movie is a film that I was so excited to watch when I was 10 years old. The original cast from the series returns in the feature film along with new but recognizable faces. Lucas Till who portrays Travis, Miley’s childhood friend and love interest. Natalia Dyer who portrays Clarissa, a fan of Hannah Montana, and goes on to star in Stranger Things as Nancy Wheeler.

Might I mention a notable appearance from Miss Taylor Swift herself. I had Crazier on repeat for months after I saw the film.

One of the most memorable scenes for me was the Hoedown Throwdown scene. I don’t really remember the dance steps though. 10 year old me probably would.