In a recent retrospective interview, Andy Cohen, the host of 'Watch What Happens Live,' opened up about some of the most memorable moments he has experienced during his 15 years on the show. Cohen discussed his interviews with media mogul Oprah Winfrey and pop icon Madonna, shedding light on both the highlights and awkward encounters that ensued.

One of the standout moments for Cohen was when he had the opportunity to interview Oprah Winfrey in 2013, marking a significant milestone for the show. The inclusion of such a renowned personality added immense credibility to the relatively new program. Describing Winfrey's appearance as a huge moment, Cohen expressed his admiration for her, stating, "I'm such a fan of Oprah."

However, Cohen couldn't resist delving into provocative and controversial topics, a trait that has long defined his career. In what Cohen now considers one of his few regrets, he asked Winfrey if she had ever "taken a dip in the lady pond." Despite Winfrey's concise response of "No," Cohen felt that he may have crossed the line by delving into such a personal inquiry.

Fortunately, Winfrey's graceful response and subsequent explanation from her friend, Gayle King, helped alleviate Cohen's unease. It turned out that Winfrey had misunderstood his reference to "the lady pond." Despite his regrettable choice in questioning, Cohen still holds Winfrey's appearance as his favorite episode, expressing gratitude for her participation on the show.

In addition to Winfrey, Cohen reminisced about his encounter with the legendary Broadway artist Patti Lupone, citing her as his favorite guest due to her unapologetic and candid nature. However, not all interactions have been smooth sailing for Cohen. He recalled a moment that landed him in trouble with Madonna, who allegedly criticized him during one of her performances. In an attempt to mend fences, Cohen sent Madonna a montage of the positive remarks made about her on the show. Although she has yet to accept an invitation to appear on 'Watch What Happens Live,' Cohen believes that she appreciated the gesture.

Reflecting on the success of 'Watch What Happens Live,' Cohen attributed it to the show's spontaneity, authenticity, and the unpredictable nature of his interviews. He also highlighted the influence of the show's unique studio space, where guests often feel at ease due to its small and intimate atmosphere. This setting, along with the presence of a bar, encourages guests to let their guard down and engage in more candid conversations, setting 'Watch What Happens Live' apart from traditional talk shows.

Cohen further mentioned a historic episode that featured Regina King and Jackée Harry, where the two guests indulged in alcohol before and during the show, leading to an entertaining and unpredictable broadcast. This experience prompted Cohen to embrace the unpredictability and chaos that can arise on 'Watch What Happens Live,' establishing the show as a platform for unforgettable late-night moments.

As 'Watch What Happens Live' celebrates 15 years on air, Andy Cohen continues to provide viewers with engaging interviews, unfiltered conversations, and memorable experiences with some of the biggest names in entertainment.