During a recent episode of The Drew Barrymore Show, Jay Leno surprised both Drew Barrymore and cohost Ross Mathews by revealing he babysat Barrymore when she was just three years old, as he was dating her aunt at the time. Leno recounted the amusing memory of bouncing young Drew on his knee, prompting Barrymore to express her surprise at not having discussed this before. She also shared her first experience appearing on Leno's Tonight Show, which was during Johnny Carson's hosting era. Mathews, who started his career as an intern on Leno's show, reminisced about their past, with Leno humorously recalling Mathews as both his favorite and most annoying intern. Leno expressed pride in both Barrymore and Mathews for their successful careers, highlighting the significance of their shared history.