Jimmy Fallon Says His ‘Mom Started Crying’ After He Underwent a ‘Free’ Major Hair Transformation in College

**Hair-Raising Tales: Jimmy Fallon and Tom Brady Reflect on Awkward Styles on The Tonight Show**

In the latest episode of *The Tonight Show*, host Jimmy Fallon took a trip down memory lane, sharing a cringe-worthy hair story that had him regretting a particularly bad haircut from his college days. This amusing revelation sparked a nostalgic conversation, especially as guest Tom Brady, the legendary retired quarterback, offered his own amusing recollections of hairstyles that evoked some tears from his mother.

During the broadcast on Tuesday, 17 March 2026, Fallon drew laughter from the audience as he unveiled a throwback photograph of Brady, who was equally amused by the hairstyle he sported at that time. Brady, who turned 48 recently, joined in the fun and reflected on the bowl cut he had because he convinced his mother that it was the hairstyle for him. “My mum used to cry when I would come home with haircuts,” he recounted, prompting chuckles from both Fallon and the audience.

Fallon seized the opportunity to recount his own hair horror story, revealing an ill-fated decision to get a perm while he was in college. He recounted how, while wandering past a group of friends getting their hair done, a young woman suggested he might like a “body wave” to give his straight hair a bit more flair. “I didn’t know what that was, but I said yes,” he confessed, clearly recalling the moment with a mix of humour and embarrassment.

What followed was a rather dramatic hair transformation. Fallon described finding himself in a rather hapless situation, with rollers in his hair and sitting under a heat lamp after saying “yes” to the free service offered by his well-meaning friend. “Before I knew it, I had the tightest perm ever,” he added, laughter echoing through the studio as he relayed the story.

Intrigued, Brady inquired whether any photographs of this hair disaster existed. Fallon, slightly sheepish, confirmed that unfortunate images were indeed out there. He then recounted the aftermath of revealing his new look to his mother, who did not react as he had hoped. “I remember going home, and my mum started crying,” he recounted. Despite his justification that the haircut was free, Fallon knew it wasn’t the reassurance she sought.

As they turned their conversation towards the present, Brady spoke about coming out of retirement to compete in the Fanatics Flag Football Classic, set to take place later this month on 21 March. His appearance on *The Tonight Show* came shortly after he was questioned about the prospect of flag football being included in the 2028 Olympics, where he responded, “I would never say never, but it is probably unlikely.”

The former NFL star reflected on the excitement surrounding younger players and their desire to represent Team USA, mentioning current stars like Patrick Mahomes and Josh Allen, who he believes are best suited to chase Olympic glory. Brady, a father of three, advised that while he wouldn’t pursue playing himself, stepping in as a coach or advisor might be a better fit for him.

The banter between Fallon and Brady highlighted the light-hearted side of famous personalities, allowing audiences to see a glimpse of them beyond the limelight. The friendly exchange encouraged fans to laugh along with their favourite stars as they shared personal experiences that resonated with many.

*The Tonight Show* continues to be a platform where celebrities can engage with familiar and relatable stories, leaving viewers entertained and often reflecting on their own similar experiences. With Fallon at the helm, there is always room for laughter, whether it be through hair disasters or sports anecdotes, ensuring a delightful viewing experience.

As Brady prepares to step back onto the field, it will be interesting to see how these nostalgic conversations shape his appearances and engagement with fans in the coming days. Meanwhile, Fallon’s penchant for sharing personal misadventures reminds everyone that even the most iconic figures have faced their fair share of hair-raising moments.