Calling out "blackface" for somebody in the 90's dressing up as Aladdin is a definite tell for somebody's political biases.
"Justin Trudeau also admitted to wearing blackface makeup to sing the Jamaican folk song "Day O" in high school for a talent show."
Source: https://time.com/5680759/justin-trudeau-brownface-photo/
> Jimmy Kimmel donned black paint over his body and used an exaggerated, accented voice to portray NBA player Karl Malone on The Man Show in 2003.
> In 2007, Sarah Silverman performed in blackface for a skit from The Sarah Silverman Program.
I don't think many people really realized blackface was problematic until sometime after 2007. Twitter started in 2006, so I imagine awareness improved in part due to twitter.