Nikki Glaser shared her experience of writing roasts, particularly her recent performance at the Netflix special 'The Greatest Roast of All Time: Tom Brady,' where she joked about Brady's divorce and financial losses. During an interview, Glaser described the process as mentally taxing, stating she needs a 'cleanse' afterward due to the negative mindset it fosters, which involves crafting potentially hurtful jokes about others. Tom Brady expressed regret over the impact of the roast's jokes on his family, particularly his children, indicating he may not participate in future roasts. Glaser acknowledged Brady's feelings, suggesting that he might not have fully considered the repercussions for his loved ones. She remarked on the surprising willingness of celebrities to be roasted, pointing out that unless they specify limits, she feels justified to go all out. Glaser's comedy aims to address taboo subjects, and her HBO special 'Someday You'll Die' continues to push boundaries in humor.