Before she was the razor-tongued Santana Lopez on Glee, Naya Rivera was just a precocious kid with a face the camera absolutely loved. Honestly, if you grew up in the 90s, you probably saw her dozen times without even realizing it. She was everywhere. One of those "everywhere" moments was a recurring guest spot that often gets overlooked. Naya Rivera in Family Matters wasn’t just a fluke; it was a three-episode run that proved, even at five years old, she could hold her own against sitcom heavyweights like Jaleel White.
It’s weird looking back now. You see this tiny girl with huge eyes and a ton of attitude, and it’s impossible not to see the blueprints for the characters she’d play later. She didn't just show up. She commanded the scenes she was in.
👉 See also: Bob Seger’s Night Moves: Why We’re Still Working on Those Memories 50 Years Later
Who did Naya Rivera play?
In 1992, Naya stepped onto the set of the Winslow household. She played Gwendolyn, the daughter of the Winslows' next-door neighbors. Now, Gwendolyn wasn't just any kid. She was a little girl with a massive crush on Richie Crawford (played by Bryton James).
She first popped up in Season 4, Episode 8, titled "Just One Date." It’s a classic Family Matters setup. Richie is young, cute, and completely oblivious to the fact that this little girl is basically obsessed with him. Naya played Gwendolyn with this hilarious, borderline-intense devotion. She was sweet, but you could tell she was the one in charge of their "relationship."
She appeared in two more episodes during that same season: "Heart Strings" and "Mama's Wedding." While she wasn't a series regular, Gwendolyn became a memorable part of Richie's early childhood arc.
That signature Naya energy
What’s wild is how much of Naya’s natural charisma was already there. Most five-year-olds on sitcoms are just there to look cute and say a "darnest things" line. Naya was different. She had timing.
There's a specific scene where she’s basically trying to mark her territory with Richie, and the way she delivers her lines is pure gold. It’s that same "don't mess with me" energy that made Santana Lopez a household name twenty years later. You can't teach that. You either have that spark or you don't. Naya had it in spades.
The child star struggle
Working on Family Matters was part of a larger whirlwind for her. Around this same time, she was coming off a main role in The Royal Family, which was supposed to be her big break until Redd Foxx tragically passed away on set.
Naya has talked about that time in her memoir, Sorry Not Sorry. She mentioned how she "fell in love with being on TV" during these early years. Even though she was so young she couldn't even read her scripts yet—her mom, Yolanda, had to recite the lines to her so she could memorize them—she was a pro. She never missed a beat.
Why her role as Gwendolyn still matters
Usually, guest spots on 90s sitcoms are just trivia. But for Naya fans, these episodes are a bittersweet look at where it all began. Seeing her as Gwendolyn reminds you that she was a veteran of the industry by the time most people "discovered" her in 2009.
She wasn't an overnight success. She was a working actor who put in the time. After Family Matters, she did The Fresh Prince of Bel-Air, Baywatch, and Smart Guy. She was a staple of the "Golden Age" of Black sitcoms.
A quick breakdown of her Family Matters run:
- Character Name: Gwendolyn
- The Vibe: Precocious, bossy, and deeply in love with Richie Crawford.
- Total Episodes: 3
- The Episodes: "Just One Date" (4x08), "Heart Strings" (4x19), and "Mama's Wedding" (4x25).
- The Year: 1992-1993
Misconceptions about her early career
Some people think Glee was her first real job. Nope. Not even close. By the time she was ten, her resume was longer than most adult actors.
🔗 Read more: Why Three Little Fishies is the Weirdest Hit Song You Probably Know by Heart
There’s also a common mistake where people think she played 3J’s sister or something similar. She didn't. She was purely the neighbor girl. It’s a small distinction, but for the die-hard fans, it counts.
Honestly, the 90s sitcom circuit was a tight-knit world. You’d see the same kids rotating through Moesha, The Bernie Mac Show, and Family Matters. Naya was a key player in that ecosystem. She was part of a generation of child actors who really shaped the look and feel of 90s television.
How to watch her episodes today
If you want to see a tiny Naya Rivera in action, you can find Family Matters streaming on platforms like Max (formerly HBO Max) or Hulu, depending on your region.
✨ Don't miss: Lottery Ticket: Why This 2010 Hood Classic Still Hits Different Today
Watching those episodes now feels a bit different. There’s a scene in "Just One Date" where she’s just being a kid, and it’s a reminder of the incredible talent the world lost. She was a natural-born performer from day one.
Next Steps for Naya Fans:
If you want to dive deeper into her early work beyond the Winslow house, I'd highly recommend tracking down episodes of The Royal Family. It was her first major role, and she earned a Young Artist Award nomination for it. It really shows off her range before she even hit first grade. Also, her memoir Sorry Not Sorry: Dreams, Mistakes, and Growing Up gives some incredible behind-the-scenes context on what it was like being a child star in that era. It’s a raw, honest look at the industry that isn't always as shiny as it looks on screen.