From: officialflagrant
Comedian Whitney Cummings recounted her experience roasting Donald Trump and their subsequent interactions. She participated in the Comedy Central Roast of Donald Trump, held in New York [01:08:01].
The Roast Experience
During the roast, Cummings made jokes about Trump’s hair and business practices [01:09:34, 01:08:08]. Trump was “dying laughing the whole time” [01:09:39]. Each roast typically has off-limits topics; for Trump, it was his wife Melania, not Ivanka [01:09:10]. Cummings had “four pages” of jokes prepared about Melania but avoided them due to this rule [01:09:13, 01:09:14].
Cummings noted that Trump is “first and foremost an entertainer” [01:07:37] and was “the number one TV star in the world” at the time [01:07:39]. She believed he would win the presidency because he understood how to “command attention,” even by not showing up to debates, which generated more attention than others who did attend [01:07:43, 01:07:52, 01:07:55]. This highlights his understanding of public perception and entertainment.
Post-Roast Interactions
After her performance, Trump pulled Cummings close, put his hand on her lower back, and told her, “That was great television” [01:09:41, 01:10:11]. Cummings felt they were “in on it together” [01:10:13]. She reflected that he did not focus on whether the jokes were funny or mean, but rather on their effectiveness as “great television” [01:09:58, 01:10:00, 01:10:03].
Later, Trump asked for Cummings’ phone number through an agent [01:10:22, 01:10:29]. However, he never called her, which left her feeling a “sense of rejection” [01:10:32, 01:34:50]. This experience contributes to discussions on comedians and politics and comedian interactions and dynamics.