Charlie Sheen was at a weird crossroads in 2001. Honestly, we all remember that era for different reasons—the baggy jeans, the transition from analog to digital, and the peak of the R-rated studio comedy. But for Sheen, it was a moment where he was trying to figure out if he was a movie star or a sitcom legend. This is where the cast of Good Advice comes in. If you haven’t seen it, the movie is basically about a disgraced stockbroker who ends up writing an advice column under a female pseudonym. It’s a classic "fish out of water" setup, but what makes it actually worth talking about twenty-five years later isn't necessarily the script. It’s the people.
You’ve got a mix of Oscar nominees and 90s sitcom royalty. It's a snapshot of a Hollywood that doesn't really exist anymore.
The Leading Man: Charlie Sheen Before the Chaos
When people look up the cast of Good Advice, they’re usually looking for Charlie Sheen. This was post-Spin City but pre-Two and a Half Men. He plays Ryan Turner. Ryan is a guy who loses everything because of one bad tip and ends up living off his girlfriend’s career. Sheen has this specific type of energy—a kind of fast-talking, slightly greasy but ultimately charming vibe—that worked perfectly for a guy pretending to be "Cindy," an advice columnist.
It's funny. Sheen's career is often defined by his off-screen antics, but in Good Advice, you see a professional actor hitting his marks with precision. He carries the movie. He’s the engine. Without his specific brand of frantic charisma, the premise would probably fall flat on its face. He had to play a man learning empathy through the letters of strangers, and somehow, he makes you believe he actually cares about Mrs. Goldberg’s plumbing problems.
Angie Harmon and the Power of the Straight Man
Then you have Angie Harmon. She plays Page Hensen. At the time, Harmon was coming off a massive run on Law & Order as Abbie Carmichael. She was the "it" girl for smart, tough, no-nonsense characters. In this movie, she’s the one who gives Ryan the job at the newspaper, not knowing he’s the one writing the column.
Her role is tricky. She has to be the romantic interest while also being the person who could realistically fire the protagonist at any second. Harmon brings a level of gravitas to a movie that could have easily drifted into pure slapstick. You believe she runs a struggling paper. You believe she’s stressed. Most importantly, you believe she’d fall for a guy who finally starts listening to people instead of just looking at ticker tapes.
The Denise Richards Connection
We have to talk about the Denise Richards factor. She plays Cindy Styne, the original advice columnist and Ryan’s girlfriend. At the time, Sheen and Richards were a massive tabloid fixture. They eventually married and had a very public fallout, but in Good Advice, they have a weird, kinetic chemistry.
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Richards plays Cindy as someone who is essentially the opposite of the "advice" she’s supposed to be giving. She’s flighty. She leaves Ryan for a tycoon in Brazil. It’s a small role, but it sets the entire plot in motion. If Cindy doesn't leave, Ryan doesn't take over her column, and we don't have a movie. It’s a bit of meta-casting that adds a layer of "Oh, I remember those headlines" for anyone watching it today.
The Supporting Heavyweights: Arkin and Estévez
The real juice in the cast of Good Advice comes from the supporting players. Specifically, Jon Lovitz and Alan Arkin.
Jon Lovitz as Barry Sherman: Lovitz is doing what Lovitz does best—playing the neurotic, slightly pathetic best friend. He’s the one who helps Ryan hide the secret. Every time the movie starts to feel a bit too much like a standard rom-com, Lovitz pops in with a line delivery that reminds you it's a comedy. He’s the king of the "slow burn" reaction.
Alan Arkin as Donald Simpson: Arkin is a legend. Period. In this movie, he plays the owner of the newspaper. Arkin doesn’t phone it in. He treats the material with a dry, cynical wit that makes the newsroom scenes feel grounded. Seeing a future Academy Award winner (for Little Miss Sunshine) trading barbs with Charlie Sheen is a reminder of how deep these early 2000s comedy benches were.
Rosanna Arquette as Cathy Sherman: Arquette is an indie darling who ended up in this mainstream comedy, and she brings a weird, wonderful energy to it. She plays Barry’s wife. It’s a smaller part, but she’s Rosanna Arquette—she brings a certain "cool factor" just by standing in the frame.
Why This Specific Cast Worked (And Why It Didn't)
Critically, Good Advice didn't set the world on fire. It has a 21% on Rotten Tomatoes. That’s rough. But if you look at the audience scores or the way people talk about it on late-night cable reruns, there’s a lot of affection there.
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Why? Because the cast of Good Advice outperformed the material.
Usually, in a mid-budget comedy, the actors are just there for the paycheck. You can smell the boredom through the screen. But here, you have actors who were all at interesting points in their careers. Barry Levinson’s production company was involved. There was a sense that this could be the next Jerry Maguire or As Good As It Gets. It didn't quite reach those heights because the script felt a little dated even for 2001, but the ensemble makes it watchable.
The Directorial Vision of Steve Rash
Steve Rash directed this. He’s the guy who did The Buddy Holly Story and Can't Buy Me Love. He knows how to handle stars. He lets the cast of Good Advice breathe. He doesn't over-edit the comedy. If Alan Arkin wants to take a five-second pause before answering a question, Rash lets the camera linger. That’s rare in modern comedies that feel like they’re edited by someone on a caffeine overdose.
The Newsroom Dynamic
The movie spends a lot of time in the offices of the "San Francisco Courier." It’s a romanticized version of journalism—desks piled with paper, grumpy editors, and the "stop the presses" trope. This setting allows the cast to play off each other in a confined space. It creates a sitcom-like familiarity that feels cozy.
Lessons From the Cast’s Career Paths
If you look at where these people went after Good Advice, it’s a fascinating map of Hollywood:
- Charlie Sheen became the highest-paid man on television.
- Angie Harmon became a staple of TNT's Rizzoli & Isles.
- Alan Arkin solidified his status as a prestige supporting actor, eventually winning an Oscar.
- Jon Lovitz remained a voice-acting and Saturday Night Live icon.
Watching them all together in one 90-minute block is like looking at a high school yearbook. Some of them became the prom king, others became the successful eccentric uncle.
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What We Get Wrong About "B-Movies" Like This
People often dismiss movies like Good Advice as "filler." But there’s an art to the mid-budget studio comedy. These movies relied entirely on the strength of their cast to pull people into theaters. Without a massive CGI budget or a superhero IP, the cast of Good Advice had to be the special effect.
They had to make you care about whether a guy was lying to his boss about being a woman named Cindy. And honestly? They did. The movie has heart because the actors took the characters seriously. They didn't wink at the camera. They played the stakes as if they were real.
Actionable Takeaways for Movie Lovers
If you’re planning to revisit this film or watch it for the first time because you’re interested in the cast of Good Advice, here is how to get the most out of it:
- Watch for the Arkin/Sheen scenes. The chemistry between a veteran character actor and a then-reigning movie star is a masterclass in contrasting styles.
- Pay attention to the 2001 aesthetics. The technology (or lack thereof) in the newspaper office is a trip down memory lane.
- Observe the comedic timing of Jon Lovitz. He’s often under-appreciated for how much heavy lifting he does in the background of scenes.
- Check out the soundtrack. It’s a very specific "early 2000s" vibe that complements the cast’s energy.
The best way to enjoy Good Advice is to view it as a showcase for a group of very talented people who were all in the same room at a very specific moment in time. It's not a masterpiece, but it’s a perfectly crafted piece of comfort food that relies on human charm rather than digital tricks.
Go find it on a streaming service or an old DVD. Skip the trailers. Just sit down and watch a group of professionals do their thing. You’ll find that even "bad" movies are pretty great when the cast is this good. Focus on the nuances of the performances rather than the predictability of the plot. You'll see a side of Charlie Sheen that got lost in the later "Winning" years—a side that was genuinely vulnerable and funny. That’s the real value of looking back at these ensembles. They remind us of the range actors have before they get boxed into specific public personas.
Check the credits next time you see a movie with a 20% rating. Sometimes, the names on the poster tell a much better story than the score on the screen.