Celebrities

Matt Damon Recalled A Calvin Klein Sales Assistant Refusing To Let Him Buy His Own Underwear After “Good Will Hunting,” And Regular People Are Tireddddd

2026-08-06 10:40
672 views

"I finally have money, and you're not letting me buy anything in your store."View Entire Post ›

    Matt Damon Recalled A Calvin Klein Sales Assistant Refusing To Let Him Buy His Own Underwear After “Good Will Hunting,” And Regular People Are Tireddddd

    “I finally have money, and you’re not letting me buy anything in your store.”

    The reason why Matt Damon and Ben Affleck’s rise to superstardom is considered so remarkable is that they literally did it entirely themselves, making it pretty impressive that they have both reached the level they’re at now.

    If you need reminding, the two first met when Ben was just 8 years old, and Matt was 10, and they lived a block and a half away from each other in Boston, Massachusetts. They were introduced through their moms, who were both teachers, and they bonded over their shared love of acting.

    The pals moved in together immediately after school as they each worked the audition circuit, and ended up opening a shared bank account after deciding that one wasn’t going to make it big without the other. This meant that if one of them managed to book a job, they deposited the cash into the joint account so that they could both afford to travel to other auditions because neither of them had any disposable cash otherwise.

    Speaking on The Bill Simmons Podcast, Ben explained: “We were going to help each other and be there for each other… It was like, ‘You’re not going to be alone. I’m not going to be alone. Let’s go out there and do this together.’”

    “As long as one of us had money, we knew the power wasn’t going to get shut off,” Matt added. “After doing [1993's] Geronimo, I probably had 35 grand in the bank. I was like, we’re good for a year."

    While they were living together, Matt was also casually attending Harvard University, and the final project in his drama class was to write a 40-page script — an assignment that turned out to be completely life-changing for both Ben and Matt. You see, after they relocated from Boston to Los Angeles, they decided to revisit Matt's script together, and it eventually became Good Will Hunting — the breakout movie that earned them both Oscars in 1998 and catapulted them to global fame.

    Reflecting on writing the movie, Matt once said: “It took us forever to write that screenplay… We were, like, unemployed, broke guys.”

    Needless to say, with their ascent to stardom also came a whole lot of money, and a resurfaced interview where Matt recalled his “I made it” moment has recently gone viral — and sparked mixed reactions.

    Speaking to Elle magazine alongside Ben for their 2023 movie Air, the duo was asked about the “first time [they] felt like [they] made it,” and something immediately came to mind for Matt. He began: “When I was a struggling actor, I think I had one pair of boxer briefs. They were less popular back then; you either had boxers or briefs.”

    “They were expensive, so I only had one pair, but I always looked forward to doing my laundry because I knew that was the day I was gonna get to wear my boxer briefs,” he went on. “So, after Good Will Hunting, I remember going to Calvin Klein and buying, like, 20 pairs of boxer briefs, and feeling like that was it.”

    “In fact, the salesperson came running out and was insisting that she give them to me,” Matt continued. “And I said: ‘No, no, you don't understand, I really need to buy these. This is a rite of passage for me,’ and she wouldn't let me buy them. She said: ‘I might get fired if they hear that you had to come in and buy underwear.’”

    “This is the weirdest thing,” Matt remembered. “I finally have money, and you're not letting me buy anything in your store. You're trying to give it to me, and I think that was probably the moment I realized things were different.”

    Earlier this week, a social media user posted this clip to X, where it has already racked up more than 6.8 million views as people share their reactions. While most people praised the relatability of Matt’s first port of call after hitting the big time, others couldn’t hide their frustration at the concept of wealthy, famous people being the ones to land freebies.

    Matt Damon reveals the exact moment he realized he'd made it

    "After Good Will Hunting, I remember going to Calvin Klein and buying like 20 pairs of boxer briefs."

    "A salesperson came running out insisting she give them to me... I said, 'No, no, no, I really need to buy these.… pic.twitter.com/AkanOxOxwE

    — ABDCHAIN (@Web3luveer) August 4, 2026
    Elle / Via x.com

    One quote-tweet reads: “This is possibly one of the most relatable things I’ve heard a celebrity say.” Somebody else quipped: “No car or mansion would replace the feeling of a fresh set of socks, boxers, and tees, man. I swear.” Another echoed: “Real. Still remember the first time I made enough money to level up the underwear drawer from Hanes to CK 😆”

    Meanwhile, another wrote: “It’s bullshit how the more money you have the less you have to buy.” Somebody else joked: “i never get this they’re literally rich they should be paying more for stuff why are we giving rich people freebies. Actually buy my underwear and clothes for me as well please !” While one more noted: “Success isn't when you can buy something. It's when people won't let you pay for it.”

    What do you make of Matt’s underpants saga? Let me know in the comments below!

    Comments