Like the movie, which turns 20 years old today, Lipnicki, who played Ray Boyd, has grown up. At 26, he's still acting, and fans still recognize him even without his ubiquitous round glasses. A week does not go by without someone quoting him his best known line -- "Did you know the human head weighs eight pounds?" -- or some version of it.
"It used to be every single day, now it's every week," he told ABC News. "And people always get the line wrong -- 'The human brain weighs 10 pounds' -- or they give the me the wrong quote from the movie -- 'Show me the money.' That was Cuba (Gooding Jr.). That wasn't me. But I don't really care. I was really lucky to be part of such a great movie."
"It changed the trajectory of my life," he added. "It’s what made me realize what I wanted to spend the rest of my life pursuing. It’s full of very happy memories."
In fact, Lipnicki was very nearly not a part of it.
He saw the fun his older sister was having at a community acting school in their Agoura Hills, California, hometown. Lipnicki asked his mom if he could try, too. She initially said no, thinking the 6-year-old was too young. But the teacher, seeing the youngster's charisma, convinced her otherwise.
Soon after, he booked a couple commercials and got a meeting with a casting associate for his first movie, "Jerry Maguire."
"I was a big fan of his," Lipnicki said about meeting Cruise for the first time, "because my parents showed me 'Top Gun.'"
"They were like real parents," Lipnicki said. "They were really, really kind to me and showed me the ropes. I felt at home. Everything felt really right -- and I’ve never lost that feeling."
Lipnicki went on to star in "Stuart Little" and its sequel, "The Little Vampire" and "Like Mike." He also appeared in episodes of "The Single Guy," "The Jeff Foxworthy Show" and "Dawson's Creek."
But as he got older, acting and those adorable round glasses took a backseat to sports and high school.
"I had this completely normal life," he said, "and then add the acting thing on top of it."
As he did before becoming a star, Lipnicki attended public school. He played baseball and basketball and, in high school, was on the water polo team. At 18, he traded in his glasses for LASIK eye surgery.
He was accepted into college and almost went.
"At the last minute I said I’m not going to be happy," he recalled. "I decided I’m going to treat [acting] like it’s school. I’m going to go to acting class. I’m going to give it a year and see how I feel. And at the end of the year, I booked a movie and never looked back."
Now, Lipnicki is like most working actors who have to audition in order to book a job. But he still gets recognized -- for better or worse.
At 19, he walked into one audition where the producer, in sunglasses and holding an unlit cigar, took one look at him and said, "You used to be cute. What happened?"
"I tried to make a joke about it," Lipnicki recalled. "And then he just let me have it for 10 minutes. He said I’m not attractive anymore and a lot of really rough stuff. I took it hard. I cried on my way home. Then I got a call from my agent. He said why were you such a jerk in there. I said, 'Excuse me?' I shut down. I actually didn't say anything."
The producer accused Lipnicki of refusing to talk about his past. His agent told him, "They're right and you're wrong."
After his anger died down -- and Lipnicki got rid of his agent -- he decided to turn the experience into comedy.
The result was a hilarious four-minute YouTube video Lipnicki made in 2014 called "You Used to Be Cute." In it, he also addresses some of the false accusations made about him over the years.
Besides the video, Lipnicki has starred in a number of online videos, independent films and a web series since making the decision to pursue acting full-time.
"I’m going to make this happen and no one’s going to stop me from doing that," he said.
And he owes it all to Crowe, Cruise and "Jerry Maguire."
Earlier this year, Lipnicki watched the film while doing a live Twitter Q&A for a friend's film club. Prior to that, he said he hadn't seen it since he was 15.
"At the time, I was dating this girl and her mom made me watch it with her," he recalled with a laugh. "What can you do?"