Lisa Ann Walter with some of her experiences as a mother. Through her experiences raising her four children, she poignantly outlined the problems that were so specific to her journey. During her appearance on The Jennifer Hudson Show on April 12, she told a hilarious anecdote about her time as Chessy in that other 1998 Disney jam, The Parent Trap. This dual role has resulted in both hilarious and frustrating trials for her boys as they start dating.
Walter, a struggling single mother in the expensive landscape of Los Angeles, took a two-year hiatus from her career to care for her eldest child. When her son saw how bored she was, he went to work. Against this backdrop, he advised her to get back into stand-up comedy—a medium that ignited her resurgence. Her experience in this juggling act between being a parent and working has affected how she sees motherhood.
Walter explained that her oldest children, daughter Delia and son Jordan, benefited from having a stronger relationship with their father’s involvement. In stark contrast, her younger twins, Spencer and Simon, have a much different experience. She noted, “My older two, the dad is great… but the younger ones didn’t have that, so I filled in for that.” This difficult dynamic has forced her to take on even more roles in her kids’ lives.
Interestingly, Walter’s sons have expressed annoyance at their mother’s iconic role. “All of my boys have said that girls have dated them specifically because Chessy is their mom,” she stated. This atypical experience has reshaped their engagements with would-be partners. It’s a hilarious glimpse into the dramatically different social worlds your parents’ fame can earn you (or banish you from) as a young person.
As frustrating as things could get, Walter would look back on the wonder and satisfaction she derived from being a mother. She joked that she went from being a teenager to a parent in warp-speed after moving to New York to pursue her acting career. “I definitely know what it’s like to be a working mother — I was doing standup comedy three days before Delia was born,” she shared.