- Harsher in Hindsight: Randy's "Andy" love ballad to Andrew Cuomo, while still hilarious and catchy, can come off as a Horrible Judge of Character after Cuomo was accused of downplaying COVID deaths and of sexual harassment by a former intern and ultimately pressured into resigning.
- Hilarious in Hindsight: In "Speaker Of The House
", Randy reviews Kevin McCarthy's less-than-impressive performance as Speaker of the House of Representatives and remarks that "I'll eat my MAGA hat if he lasts one year." Seven months after this video was posted, McCarthy was ousted by a motion to vacate the chair after a tenure lasting from early January to October of the same year, eventually going on to resign as a member of the House entirely - and is now officially known as the third-shortest serving Speaker in US history. Comments on the youtube page were quick to congratulate Randy on not needing to eat his hat. - Unintentional Period Piece: "Any Dem Will Do!" has Randy moderating the 2020 Democratic debate and singing about his uncertainty over who to support. Three of the candidates featured in the video (Pete Buttigieg, Amy Klobuchar, and Tom Steyer) had already dropped out of the race by the time it was posted, making it instantly dated.
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