Reese Witherspoon is a household name, celebrated for iconic roles like Legally Blonde and Wild, but two of her most underrated films are quietly waiting to be rediscovered.

“How Do You Know” and “The Man in the Moon” are often overshadowed by her blockbuster hits, yet they showcase her versatility as an actress and storyteller.

From romantic comedies that blend humor with heartfelt drama to animated gems that tug at the heartstrings, these movies deserve a second look. Here’s why you need to binge them now.

1. How Do You Know: The Romantic Comedy That’s Better Than You Remember

Directed by James L. Brooks, How Do You Know (2010) stars Reese Witherspoon as a single mom navigating love and career while balancing the chaos of her ex-husband’s (Paul Rudd) infatuation with her sister (June Diane Raphael).

The film’s supporting cast includes Owen Wilson as a charming but career-obsessed athlete and Jack Nicholson as his no-nonsense father.

Critics initially dismissed the movie as a “messy” ensemble piece, but its blend of wit, emotional depth, and Witherspoon’s understated performance makes it a hidden treasure.

The film’s strength lies in its exploration of love’s unpredictability. Witherspoon’s character, Sarah, is a woman who’s lost her spark after a messy divorce, but her journey—from self-doubt to rediscovering joy—is subtly powerful.

Meanwhile, Nicholson’s monologues on life’s uncertainties (delivered with his signature gravitas) and Wilson’s comedic timing elevate the film far beyond a typical rom-com. The soundtrack, featuring classic hits by artists like Carole King, adds to its timeless appeal.

2. The Man in the Moon: A Heartfelt Animated Gem You’ll Cry Over

Released in 2011, The Man in the Moon is an animated family film that’s often forgotten in Witherspoon’s filmography, but its emotional depth and creative storytelling make it a standout.

Directed by Will Gluck, the movie follows a lonely boy (voiced by Kodi Smit-McPhee) who discovers a magical world after his mother (Witherspoon) falls ill. The film’s visual style, blending hand-drawn animation with live-action, creates a whimsical yet poignant atmosphere.

Witherspoon voices the character of Alice, a woman grappling with grief and the fear of losing her son. Her performance is understated but profoundly moving, showcasing her range beyond her usual roles.

The film’s themes of love, loss, and the power of imagination resonate deeply, especially in its hauntingly beautiful third act.

While critics panned it upon release for being “too slow” or “too sad,” its quiet moments of hope and connection have since drawn a cult following.

3.Why These Movies Are Overlooked—and Why That’s a Mistake

Both films were released during a period when Witherspoon was transitioning from blockbuster comedies to serious dramas (like Water for Elephants and Prim & Proper).

How Do You Know faced backlash for its “scattered” plot, while The Man in the Moon struggled to find an audience amid bigger animated hits like Tangled and Toy Story 3. Yet, their flaws are overshadowed by their strengths.

How Do You Know benefits from a stacked cast and Brooks’ knack for balancing humor and heart, while The Man in the Moon offers a rare animated film that doesn’t shy away from mature themes like mortality and mental health.

Both also highlight Witherspoon’s ability to play layered, nuanced roles—proof that she’s more than just a “sassy blonde” icon.

4. Rediscovering How Do You Know: A Love Story for the Real World

What makes How Do You Know so refreshing is its refusal to stick to rom-com tropes. The relationships here are messy, flawed, and unscripted. Witherspoon’s Sarah isn’t a “perfect” heroine; she’s pragmatic, insecure, and at times selfish.

Similarly, Wilson’s character isn’t a typical “hero”—he’s a man who must confront his fear of commitment, played with raw vulnerability.

The film’s climax, which sees the characters making imperfect choices, feels refreshingly realistic. Unlike movies that wrap everything up in a tidy bow, How Do You Know leaves room for ambiguity, mirroring life’s unpredictability. This authenticity is why it’s a must-watch for anyone tired of formulaic love stories.

5. Why The Man in the Moon Deserves a Second Chance

Animated films for kids often prioritize humor over emotional depth, but The Man in the Moon dares to be different.

The story’s emotional core—centered on a mother’s love and a child’s fear of losing her—is rendered with surprising subtlety. Witherspoon’s voice work is a standout; her quiet moments of grief and hope feel intimately personal.

The film’s animation, while divisive at first, becomes a strength as it progresses. The moon’s inhabitants, with their quirky designs and poetic dialogue, add a layer of whimsy that contrasts with the story’s darker themes.

Scenes like the haunting “Lullaby” sequence, where Alice’s voice echoes through the cosmos, are cinematic masterpieces that linger long after the credits roll.

6. Where to Watch and Why You Shouldn’t Wait

Both films are currently available on streaming platforms like Amazon Prime and Hulu. How Do You Know is a perfect rainy-day watch, blending laughter with introspective moments, while The Man in the Moon is ideal for a cozy family movie night.

For fans of Witherspoon, these films offer a chance to see her in roles that challenge her range. For casual viewers, they’re proof that not every “hidden gem” is a B-movie curiosity—they’re just movies that history overlooked.

7. The Final Verdict: These Films Are More Than Just “Forgotten”

Revisiting How Do You Know and The Man in the Moon isn’t just about nostalgia—it’s about appreciating stories that were ahead of their time.

In an era where streaming platforms drown us in content, these films remind us that sometimes, the best movies are the ones that make you think, laugh, and cry without needing a superhero or a franchise to back them up.

So grab some popcorn, queue these up, and rediscover why Reese Witherspoon is more than just a name from the 2000s—it’s a career built on stories worth revisiting. Your “must-watch” list won’t regret it.