
This list was first published in 2018 and has been updated since then. Rob Reiner passed away on December 14, 2025, at the age of 78.
Most directors experience both successes and failures, but Rob Reiner’s career has been an extreme rollercoaster. He effortlessly delivered smart, popular films at the height of his career, then later made movies that seemed surprisingly misjudged. While you might call him a versatile director, it doesn’t quite capture how he created films as assured as When Harry Met Sally, as hilariously chaotic as This Is Spinal Tap, or as uniquely balanced in tone as The Princess Bride. Because of these huge swings, it’s hard to neatly categorize his work.
Like Ron Howard, Rob Reiner started his career in television, and many people still remember him fondly as ‘Meathead’ from All in the Family. He’s also well-known for his liberal political views, which were famously satirized on South Park years ago. For about ten years, Reiner created films reminiscent of Frank Capra and Billy Wilder. Though his later work didn’t quite reach those heights, he recently showed a desire to explore new and different projects, which helped him recapture some of his earlier success.
You’ve likely forgotten many of the films near the end of this list. However, the top seven or eight are much more memorable, and people often argue about which one is truly the best.
21.
North (1994)
It’s strange – the review of the movie North, particularly Roger Ebert’s famously scathing one where he repeatedly stated his intense dislike, is more famous than the film itself. And director Rob Reiner got lucky that the review generated any attention at all. Even now, 25 years later, North is just as bad as Ebert described – a misguided idea brought to life in a weak and uninspired way. Reiner tries to blend lightheartedness, satire, and old-fashioned sentimentality, but the result is almost unwatchable. To make matters worse, Bruce Willis’s performance as the Easter Bunny is even less appealing than his work in Hudson Hawk. In fact, Ebert might have actually been too kind in his review.
20.
The Magic of Belle Isle (2012)
Later in his career, director Rob Reiner made films about older people dealing with loss and figuring out their next steps. After the success of The Bucket List in 2007, he worked with Morgan Freeman again on The Magic of Belle Isle, a very sentimental story about a writer struggling with grief and writer’s block. The writer, now in a wheelchair and mourning his wife, moves to a quiet town and ends up living next door to the energetic Virginia Madsen and her three unbelievably cute daughters. The film relies heavily on the actors’ charisma to overcome a predictable and cliché-filled plot. While older audiences deserve to see more films that reflect their experiences, they deserve a much better movie than this one.
19.
Alex and Emma (2003)
Around the time you started questioning Reiner’s vision, this movie appeared. It’s a fairly predictable romantic comedy where a novelist (Luke Wilson) needs to write a book in 30 days to settle a debt with the Mafia – a strange premise, to say the least. He enlists a stenographer (Kate Hudson) to help, and the story unfolds as they act out scenes for the book they’re creating. It feels like a try at something clever like The Princess Bride, but the leads have no spark, and Reiner directs it without much enthusiasm. Ultimately, this film won’t leave you longing for the classic rom-com experience.
18.
The Story of Us (1999)
Rob Reiner’s When Harry Met Sally was a classic romantic comedy, but he aimed for something more complex with The Story of Us: a realistic look at a marriage going through a difficult time. Unfortunately, the film doesn’t capture the same insightful feel as his earlier work, and its leads, Bruce Willis and Michelle Pfeiffer, feel more like characters in a TV show than real people. The movie jumps between flashbacks to show the ups and downs of their relationship. After years of success, The Story of Us was one of a string of disappointing films for Reiner, suggesting he was losing his ability to connect with relatable, universal stories.
17.
And So It Goes (2014)
Reiner and Michael Douglas first charmed audiences together in The American President. Their second collaboration, And So It Goes, is a much less successful romantic comedy. Douglas plays a grumpy, self-centered real estate agent whose unpleasant behavior is explained by the loss of his wife. After a predictable and complicated plot, he finds a chance at happiness with a granddaughter he never knew existed. Diane Keaton plays his widowed neighbor, who cautiously agrees to help him raise her, and, predictably, begins to fall for him. Despite featuring two talented actors, And So It Goes is a frustratingly saccharine comedy that avoids exploring genuine emotion or offering any real depth.
16.
Rumor Has It (2005)
Trying to evoke the spirit of The Graduate sets a high bar, and Rumor Has It unfortunately falls short, especially considering the troubled production – the original director, Ted Griffin, was replaced by Reiner. The film centers on Jennifer Aniston, a New York Times obituary writer, who uncovers a potential connection between her grandmother (Shirley MacLaine) and the iconic Mrs. Robinson, and subsequently becomes involved with a man resembling Benjamin Braddock (played here by Kevin Costner). While the constant references to The Graduate suggest a similarly clever and biting story, Rumor Has It doesn’t bother with any real depth. It’s a forced, awkward comedy that squanders the talents of its strong cast, including a young Mark Ruffalo during his romantic comedy phase. Ultimately, Rumor Has It relies too heavily on the comparison to a much better film.
15.
Ghosts of Mississippi (1996)
This film perfectly illustrates a frustrating trend in ’90s movies about the Civil Rights Movement, as noted by Godfrey Cheshire: they often portrayed white characters as the heroes who fought and won the battle for racial justice. This movie is a prime example, featuring Alec Baldwin as a determined figure bringing Medgar Evers’s killer to justice, with Whoopi Goldberg providing emotional support. It’s a remarkably simplistic and uninspired take on a complex history, and it arrived late in the game – audiences were quickly losing interest in these types of stories. Interestingly, looking back, James Woods’s intensely hateful performance feels eerily similar to his public persona today.
14.
Spinal Tap II: The End Continues (2025)
After 41 years, a sequel to the beloved comedy finally arrived, and it definitely shows its age. Most of the original cast returns – impressively, a large number are still with us – but the spark of spontaneous humor that made the first film so special is missing. This sequel feels sluggish and relies heavily on jokes and ideas from the original, but without the same energy. The movie struggles to develop its plot – even something as simple as a running gag about cheese feels unresolved – and limps through its brief runtime. It’s not necessarily bad, but it barely registers as a film. The one bright spot? Paul McCartney. His hilarious extended cameo, playing a version of himself who offers unwanted advice, provides a much-needed burst of energy and deserves its own show.
13.
Flipped (2010)
It takes a while to find the gems in Rob Reiner’s film work, doesn’t it? This movie is actually better than some of the predictable romantic comedies he’s made – it’s a sweet coming-of-age story about the innocent ‘love’ between two kids from elementary to middle school. It’s so sincere and wholesome that it’s hard to dislike, though it’s also a bit bland and cheerful. Reiner doesn’t have the same spark he did with films like Stand by Me, and this story feels a little too safe and polished. Flipped isn’t a bad movie, but it’s one you’ll likely forget quickly.
12.
Shock and Awe (2018)
Despite tackling an important story, the movie Shock and Awe feels disappointingly flat. It follows reporter Jonathan Landay (Woody Harrelson) and his colleague Warren Strobel (James Marsden) as they try to uncover the Bush administration’s misleading claims leading up to the Iraq War. Like Reiner’s previous film LBJ, it’s based on real events and explores themes relevant to today, such as the importance of a free press and the dangers of corruption. While Harrelson and Marsden deliver strong performances, the film doesn’t quite reach the heights of classics like All the President’s Men or even the more recent The Post. Everyone involved clearly cares about the story, but the movie’s unremarkable style ultimately weakens its impact. Shock and Awe ultimately feels like a reminder of how frustrating it can be to navigate a world filled with misinformation.
11.
Being Charlie (2016)
This is arguably Rob Reiner’s most autobiographical film. It tells the story of a wealthy Hollywood teenager (Nick Robinson) battling addiction, who repeatedly runs away from rehab until he meets a girl who seems to make a difference. Co-written with Reiner’s son, Being Charlie feels raw and honest, especially when depicting Charlie’s difficult relationship with his overbearing mother and emotionally distant father (who is campaigning for governor in the film). These moments are the strongest parts of the movie, but the film often drifts into a predictable romance. However, it’s refreshing to see Reiner attempting something different and personal.
10.
LBJ (2017)
In 2016, two films offered different perspectives on the Kennedy assassination. Jackie explored the tragedy through the eyes of Jackie Kennedy (played by Natalie Portman), while LBJ focused on Lyndon B. Johnson, Kennedy’s vice president, and his feelings of being overlooked, as well as the immense pressure he faced after Kennedy’s death. Though released nearly a year apart, both films are compelling when considered together, as they examine how figures connected to the Kennedy myth reconciled the public image of JFK with their own realities. However, LBJ is a fairly typical modern biopic, concentrating on the period surrounding Kennedy’s assassination and Johnson’s efforts to pass the Civil Rights Act. While Woody Harrelson brings energy to the role of the 36th president, the film doesn’t fully capture his complexity. LBJ feels low-budget, with unconvincing sets and makeup, and often feels like a simplified history lesson. What does redeem the film, to some extent, is its look at the legislative process—similar to Lincoln—showing how bills become laws. Still, it’s hard to imagine anyone other than director Rob Reiner tackling this story.
9.
The Bucket List (2007)
Despite a tendency towards sentimentality, director Rob Reiner delivers a surprisingly effective film, especially with the combined star power of Jack Nicholson and Morgan Freeman. This heartwarming comedy follows two men, both diagnosed with lung cancer, as they embark on a journey to fulfill their life goals. It essentially launched the trend of comedies focused on older characters – though Grumpy Old Men came before it. While the film isn’t perfect, Nicholson and Freeman are undeniably captivating. Interestingly, this remains Nicholson’s last major movie role, appearing over a decade ago, with only a brief appearance in the 2010 film How Do You Know since then.
8.
Stand by Me (1986)
Stephen King’s story, The Body (which this movie, Stand by Me, is based on), held personal meaning for him, drawing on memories from his own childhood. Director Rob Reiner also felt a strong connection to the film, telling Variety it was the first time he’d created something that truly reflected his own personality – a blend of sadness, humor, and thoughtful reflection. He admitted he was taking a risk with this more personal approach. After making comedies like This Is Spinal Tap and The Sure Thing, Reiner seemed drawn to the emotional depth and nostalgic feel of Stand by Me. Of his early films, this adaptation – about four young friends (Wil Wheaton, River Phoenix, Corey Feldman, and Jerry O’Connell) searching for a dead body – best captured his own sensibilities. While other films explore childhood more profoundly, Stand by Me remains a beloved classic for those who grew up in the 1980s – a fitting place for a movie so focused on remembering the past with fondness.
7.
The Sure Thing (1985)
Before many of the typical raunchy comedies of the 1980s, The Sure Thing stood out for its heartwarming approach. It proved that director Rob Reiner could create a sweet and funny movie, as opposed to just relying on crude humor. The film follows a teenager (a 16-year-old John Cusack) who journeys to California hoping to meet a girl, but unexpectedly falls for the friend who accompanies him (Daphne Zuniga). It’s a simple, feel-good comedy, and Reiner skillfully avoids making it overly sentimental. Cusack is perfectly cast, embodying the charm needed to move the romantic comedy genre forward.
6.
Misery (1990)
In early 1990, just before the release of Misery, director Rob Reiner recalled people constantly telling him to “keep making those kinds of films” after the success of When Harry Met Sally. He wondered how audiences would react to Misery, which was a significant departure for him. After years of making comedies, he wanted to challenge himself with Stephen King’s darkly funny story about a novelist (James Caan) trying to change his writing style, and his obsessive, dangerous fan, Annie Wilkes (Kathy Bates). Reiner was at a point in his career where he seemed capable of effortlessly succeeding in any genre. Misery continues to be relevant today, showing the complicated dynamic between artists and their fans, who often expect artists to prioritize their desires. Think of all the modern-day “Annies” who now have a voice thanks to social media. Kathy Bates’s brilliant and terrifying performance in Misery won her an Academy Award – the only Oscar ever awarded to a Rob Reiner film.
5.
The American President (1995)
With The American President, director Rob Reiner concluded a successful period of making popular and critically acclaimed films. He again collaborated with Aaron Sorkin, the screenwriter of A Few Good Men, to create a hopeful and mature love story. The film stars Michael Douglas as a widowed president who falls for Annette Bening, an enthusiastic environmental advocate. While a bit of a fantasy about both progressive politics and the power of love, the film is smart and believable thanks to its thoughtful approach. Douglas, known for playing flawed characters, delivers a charming and optimistic portrayal of the president, and his chemistry with Bening feels like classic Hollywood. The film’s blend of personal stories and political maneuvering foreshadowed Sorkin’s later success with The West Wing, and even featured Martin Sheen – who played the president’s chief of staff here – as the President himself in that TV series.
4.
A Few Good Men (1992)
Rob Reiner had proven he could handle both comedies and serious dramas, but this film showcased a different side of him: the skilled director who delivers a classic, star-studded story, complete with a somewhat cheesy but surprisingly powerful courtroom climax. While Aaron Sorkin’s script doesn’t feel very realistic – it’s a very Hollywood take on the military – Reiner wisely lets Tom Cruise, Demi Moore, and especially Jack Nicholson, shine in the film’s most dramatic scenes. It’s pure entertainment, and incredibly captivating despite its obvious artificiality.
3.
When Harry Met Sally (1989)
Rob Reiner directed many successful films in the 1980s and 90s, but When Harry Met Sally remains his most culturally significant work. While his other films have memorable moments, this romantic comedy uniquely captured the anxieties of dating, and the arguments between Harry (Billy Crystal) and Sally (Meg Ryan) still resonate today. The film was inspired by the real-life friendship between Reiner and Nora Ephron, who based the characters on their own experiences and stories. Set in New York City and reminiscent of Woody Allen’s films with its clever dialogue, When Harry Met Sally stood out as a mature and insightful love story during a time dominated by teen comedies and big-budget action films. The film showcases Reiner’s ability to create a genuinely charming, intelligent, and funny romantic movie that feels perfectly confident in its approach. It’s a testament to his skill, as it’s surprisingly difficult for other filmmakers to achieve the same effortless quality—and Reiner himself struggled to replicate it later in his career.
2.
This Is Spinal Tap (1984)
Rob Reiner’s brilliant first film started with just a four-page outline and very little planned dialogue. It began as a playful idea to satirize a struggling fictional metal band. Trying to explain why “This Is Spinal Tap” is funny feels pointless – it not only invented the mockumentary genre but also popularized a spontaneous, improvisational comedy style that now dominates Hollywood. So, let’s focus on the film’s unexpected emotional depth. The characters – David St. Hubbins, Nigel Tufnel, and Derek Smalls – aren’t simply unpleasant; their endearing naiveté, unwarranted confidence, and surprising vulnerability elevate them to figures of genuine tragedy. Reiner himself plays Marty Di Bergi, the documentarian following the band, and he’s the perfect, understated foil. When you rewatch “This Is Spinal Tap,” pay attention to Reiner’s performance – he never breaks character or signals the jokes, which makes the band’s hilarious absurdity even funnier.
1.
The Princess Bride (1987)
Reiner truly shines in this film, capturing a genuine and warm perspective that’s often missing in his other work. He expertly balances heartfelt emotion with a playful, knowing irony – a bit like the classic humor of Bob and Ray. When he loses that touch, his movies can be difficult to watch, but when he nails it, as he does here, the result is magical. This film is a clever take on storytelling itself, playfully poking fun at fairy tale clichés while still embracing their charm – it’s both a satire and a perfect example of the genre. And with a cast of ten unforgettable characters, including a surprisingly touching performance from Andre the Giant, it’s a truly remarkable achievement. It’s hard to believe anything could top it.
Grierson & Leitch are frequent writers and podcasters about movies. You can find them on Twitter or at their website.
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2025-12-16 23:59