Judy Greer has a vivid memory from the early days of her career: standing at a pay phone in the lobby of New York’s Roosevelt Hotel, too broke to retrieve her car from the valet, while Matthew McConaughey quietly overheard her distress and handed her $20. The story, shared in a recent Entertainment Tonight interview, surfaces as The Wedding Planner marks its 25th anniversary this year.
“I valeted my car; I didn’t know any better,” Greer said. “I didn’t have enough money to get my car out of the valet because I was so broke. I was on the pay phone in the lobby, calling my friend Sean Gunn, and Matthew McConaughey overheard me and gave me $20. I was so mortified, but also: my hero.”
The table read at the Roosevelt preceded production on the 2001 romantic comedy directed by Adam Shankman, which starred Jennifer Lopez as a San Francisco wedding planner who falls for a client played by McConaughey. Greer played Lopez’s colleague and friend Penny. The film earned $94 million worldwide and launched McConaughey’s run as one of Hollywood’s most bankable rom-com leads.
Greer spoke warmly about the experience on set. “I loved seeing him in hair and makeup every morning, because he had pajamas on and a Yerba mate. I haven’t worked with him since, but I have a feeling not much has changed.” For Greer, the film opened doors she hadn’t anticipated. “I couldn’t believe it,” she said. “In some ways, I didn’t really understand what a big deal it would be.” The role led to further rom-com work, including 13 Going on 30 and 27 Dresses.
McConaughey followed The Wedding Planner with How to Lose a Guy in 10 Days, Failure to Launch, Fool’s Gold, and Ghosts of Girlfriends Past — a rom-com stretch that crossed or approached the $100 million mark each time. He later walked away from the genre entirely, deliberately turning down projects to reset his career, a pivot that critics and the actor himself eventually dubbed the “McConaissance.”
On a potential reboot, Greer said she loves the original and finds it holds up — but questioned the industry’s appetite for revisiting existing properties. “Why do we have to keep rebooting everything?” she said, adding she’d participate as long as she gets to be in it.
