Finding the right info on the cast of Undercover Angel is actually trickier than you’d think because there are a few different movies with that name floating around. Most people, however, are looking for the 1999 family drama. It’s one of those "Sunday afternoon on cable" classics that stuck with people. It’s sweet. It’s a little bit cheesy. Honestly, it’s exactly what you expect from a late-90s indie flick about a guy who unexpectedly has to look after a kid.
The movie stars Yasmine Bleeth and Dean Winters. If you grew up in the 90s, you know Bleeth from Baywatch. This was a pivot for her. She wasn't running on a beach; she was playing a mother. Dean Winters, who most people now recognize as "Mayhem" from the Allstate commercials or Vulture from Brooklyn Nine-Nine, plays the lead, Harrison. It’s weird seeing him so young and... well, less chaotic.
The Core Cast of Undercover Angel
Dean Winters carries a lot of the emotional weight here. He plays Harrison, a struggling writer. He’s cynical. He’s a bit of a loner. Then he gets stuck babysitting a little girl named Holly. It sounds like a cliché because, frankly, it is. But Winters brings a certain grit to it that keeps it from being too sugary.
Emily Mae Young plays Holly. She was the "it" kid for a minute there. You probably remember her from the "Welch's Grape Juice" commercials or the show Step by Step. She had that specific 90s kid energy—precocious but not annoying. Her chemistry with Winters is the only reason the movie works. If the kid is bad in a movie like this, the whole thing falls apart. She wasn't. She was great.
Then there’s Yasmine Bleeth. She plays Holly’s mom, Holly Anderson. (Yes, the mom and daughter have the same name in the script, which is a choice). Bleeth was at the height of her fame here. She brings a warmth to the role that people didn't always give her credit for back then. People dismissed her as just a TV star, but she holds her own in the more dramatic scenes.
The supporting cast is a bit of a "who’s who" of Canadian and American character actors from that era:
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- Casey Kasem: Yes, the legendary radio host. He plays himself. It’s a small cameo, but for fans of his countdown, it’s a fun Easter egg.
- Alexander Chapman: Plays Rex.
- David Alan Grier: He has a role as Dan. Grier is a comedic powerhouse, and seeing him in a more grounded family drama is always interesting.
- James Earl Jones: He provides the voice of the "Angel." You can't go wrong with that voice. It adds a layer of gravitas to a movie that could have otherwise felt very "low budget."
Why the Casting Worked (and Why It Didn't)
The 90s were a weird time for independent film. Everyone was trying to find the next Jerry Maguire. You had these mid-budget movies that focused on human connection rather than explosions. The cast of Undercover Angel reflects that.
Dean Winters was an inspired choice. Usually, these roles go to "softer" actors. Winters has a sharp face and a raspy voice. He looks like he belongs in a police procedural (which is where he ended up, in SVU and Oz). Putting a "tough guy" in a room with a six-year-old girl is a classic trope for a reason. It creates instant conflict.
Emily Mae Young was arguably the biggest draw at the time. Child stars have a short shelf life. She was everywhere in 1999. Her ability to deliver lines without sounding like she was reading a script was rare.
The movie was directed by Bryan Michael Stoller. He’s known for these kinds of family-centric stories. He has a knack for getting natural performances out of kids, which is notoriously hard. He didn't over-direct Young; he let her be a kid.
What People Get Wrong About the Movie
A lot of people confuse this movie with the 2017 film Undercover Angel (also known as An Angel's Christmas). That’s a completely different cast. If you’re looking for Katherine McNamara or Judd Nelson, you’re looking for the wrong decade.
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The 1999 version is the one that people remember most fondly because of the James Earl Jones connection. His voice is unmistakable. Even if you don't see him on screen, his presence looms large. It gives the film a "magical realism" feel. It’s not quite a fantasy movie, but it’s not strictly a drama either. It lives in that middle space.
Another misconception is that it was a big theatrical hit. It wasn't. It found its life on VHS and DVD. It’s the kind of movie you'd find in a bargain bin at Blockbuster and end up watching five times because it was "comfy."
The Impact of the Cast Today
Where are they now? It’s a question fans always ask.
Dean Winters is doing better than ever. Between 30 Rock and the Allstate ads, he’s a household face. He’s moved far away from the "struggling writer" archetype.
Yasmine Bleeth largely stepped away from the spotlight in the early 2000s. Her career took a hit due to personal struggles, which she’s been open about in the past. For many, Undercover Angel represents one of her last major leading roles before she retreated from Hollywood.
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Emily Mae Young also left the industry. She didn't follow the path of many child stars into adult acting. She seemingly chose a private life, which honestly, is probably the healthier move. It makes her performance in this movie feel like a time capsule.
Actionable Insights for Fans and Collectors
If you're trying to track down this movie or learn more about the production, here are a few things to keep in mind:
- Check the Credits: Ensure you are looking for the 1999 version directed by Bryan Michael Stoller. If the box art doesn't have Dean Winters or Yasmine Bleeth, you’ve got the wrong one.
- Streaming Is Hit or Miss: Because it was an independent production, it jumps around streaming services. It often pops up on ad-supported platforms like Tubi or Pluto TV.
- Physical Media: The DVD is actually somewhat of a collector's item for fans of 90s nostalgia. Look for the "Feature Films for Families" versions, as they were the primary distributors.
- The Soundtrack: The movie features a few catchy tunes that are very "of the era." If you like that late-90s acoustic pop sound, it’s worth a listen.
The cast of Undercover Angel managed to turn a relatively simple script into something memorable. It’s a testament to the fact that you don't need a hundred-million-dollar budget to tell a story that sticks with people for twenty-five years. You just need a "Mayhem" actor, a "Baywatch" star, and the voice of Darth Vader.
To see the film today, your best bet is searching for "Undercover Angel 1999" on secondary market sites or digital rental stores. Verify the runtime is approximately 91 minutes to ensure you have the correct version. For those interested in the technical side, the cinematography by David Lewis is worth noting for its use of natural light, which was a hallmark of 90s indie dramas.