25 best award show hosts
By Reed Gaudens
22. Rosie O’Donnell
Show: 42nd Annual Grammy Awards (2000)
Memorable Moments: Over the years, the court of public opinion has ebbed and flowed regarding Rosie O’Donnell, but in the late ’90s and early aughts, she was basically everywhere, including on her eponymous daytime talk show. As the host of the Grammy Awards in 2000, she helped ring in a new era of pop music in the new millennium, which was a reinvention of teen pop. However, after J. Lo took the red carpet in the dress seen ’round the world, nothing Rosie could have said could have topped that fashion jaw-dropper.
Public Reception: Unfortunately, O’Donnell’s turn as the host of the 42nd Annual Grammy Awards didn’t earn her any awards. A review of the show from Entertainment Weekly marked O’Donnell as the lowest point of the ceremony. The article claims that her jokes ranged from the stereotypical mocking of Puff Daddy’s name (he later had it coming though with all of those moniker changes) to the double standard of negatively commenting on Jennifer Lopez’s dress and praising Ricky Martin’s tight leather pants. At least she wasn’t an overtly mean-spirited host.
Why They’re One of the Best: Regardless, Rosie O’Donnell will always be one of the best award show hosts of the Y2K generation. She might not have been everyone’s cup of tea, but her comic stylings were often palatable for the whole family. And perhaps what’s most vital here, O’Donnell showed deserved kindness to Britney Spears, who wasn’t (and isn’t) frequently afforded the luxury of stepping into a room and being treated fairly. Maybe the best thing a host can do is step back, be nice and let the stars of the hour shine.