Lindsey Lohan — David Letterman

With her complex career trajectory, Lindsey Lohan faced a challenging situation when she appeared on The Late Show in 2013. Sensibly, she had requested the production team to avoid certain sensitive topics during the interview. Regrettably, David Letterman chose to disregard her wishes entirely. Throughout the interview, he consistently brought up the rehab facility she intended to seek help from, probing into her personal life by asking if she had stolen things and how she managed her finances. Despite Lindsey's repeated pleas to shift the conversation to more appropriate topics, Letterman persisted in dwelling on these sensitive issues, pushing the young star to the brink of tears.

The episode underscored the importance of talk show hosts in celebrity interviews, emphasizing their responsibility to respect guests' boundaries and sensitivities, while also highlighting the power dynamics at play. Letterman's failure to do so brought attention to the need for more considerate and empathetic interviewing practices in the entertainment industry.

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