What Retirement Might Look Like for the ‘Clueless’ Characters
Written by
Stacy Sare Cohen
Edited by
Brendan McGinley
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Retirement? Ugh. As if!
On the heels of the movie of the same name, “Clueless” is a teen sitcom which aired from 1996 to 1999 on ABC and UPN, following the rich, superficial and well-intentioned Beverly Hills teenager, Cher Horowitz (Rachel Blanchard, picking up the role from the film’s Alicia Silverstone), whose life revolved around her friends at the fictional Bronson Alcott High School, fixing social dilemmas, trips to the mall and a haute couture designer wardrobe.
Her best friend, Dionne Davenport (Stacey Dash), shared Cher’s fashion sense and zeal for trips to the mall. After matchmaking two teachers in hopes of getting better grades, they befriended a recent transplant student from New York, Tai Frasier (Heather Gottlieb, in a role originated by Brittany Murphy). Mel’s former stepson, Josh Lucas (David Lascher, taking over from Paul Rudd), challenged Cher’s superficial priorities until he began developing feelings for her that she returned.
Nearly 30 years have passed since the show’s final episode. Let’s imagine what retirement would look like for the “Clueless” characters in 2026.
Cher Retired With a Paid-Off Mansion and a Strong Portfolio
Cher grew up in a sprawling mansion off Sunset Boulevard with her father, Mel (Michael Lerner), a high-powered litigator, who gave her carte blanche resources — an American Express Gold Card, a brand-new Jeep Wrangler and a computerized closet that sorted every outfit she owned. At his advice, Cher opened a philanthropic consulting firm and contributed regularly to her 401(k) and Roth IRA while growing her inherited trust fund.
With long-term compounding, substantial retirement savings, investments and her Beverly Hills home paid in full, she has several million dollars in equity. She lives a comfortable retirement that matches her lifestyle, and devotes her spare time — which she has much more of now that The Mighty Mighty Bosstones have stopped performing — to community organizations.
Dionne Invested in Real Estate and Has Consistent Retirement Savings
After earning a degree in fashion marketing, Dionne built a long career in luxury fashion marketing before being promoted to creative director. She and Murray married and invested in Los Angeles real estate, first buying a home in Studio City and later, a more expensive property in the Hollywood Hills, worth millions.
Her 401(k), Roth IRA and brokerage investments grew alongside her real-estate portfolio, providing a strong retirement foundation. Social Security benefits supplemented their income, allowing them to own homes in Los Angeles and Palm Springs.
Tai Retires Comfortably After a Stable Career
Tai built a steady career as a graphic designer and illustrator. She contributed to her retirement accounts consistently with an employer match and purchased a modest home in Pasadena, CA, at a great interest rate.
Her 401(k), Roth IRA, brokerage account and home equity grew into a solid retirement plan. Her retirement income is modest compared to her friends, but Social Security benefits and conservative investment withdrawals allow her to live within her means, with occasional splurges that suit her lifestyle.
Josh Marries Rich and Benefits From Retirement Savings
Josh established a long-term career as a public-interest attorney, specializing in civil rights and environmental law cases. Although not a high-powered litigation attorney like Mel, he contributed regularly to his 403(b) and Roth IRA and earned a nonprofit pension.
After marrying Cher and combining their finances, which included a mortgage-free Beverly Hills home, Josh’s pension, Social Security and joint investment income would give him a solid retirement.
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