Penn forced a terrified Jonathan Richman to perform his Velvet Underground tribute song directly for Lou Reed.
The episode of 'The 500 with Josh Adam Meyers' features comedian and magician Penn Jillette discussing Lou Reed's 'Transformer'. Host Josh Adam Meyers introduces the album and his guest. Penn Jillette immediately establishes his credentials as a superfan and close personal friend of Lou Reed, having been president of the Velvet Underground fan club. He describes how 'Walk on the Wild Side' was a transformative moment for him as a teenager in rural Massachusetts, introducing him to New York's underground culture. Penn analyzes the album's context, explaining that Lou Reed was a doo-wop fan at heart who wanted to tell gritty short stories in a pop format, influenced by his teacher Delmore Schwartz. He contrasts this with John Cale's avant-garde, John Cage-inspired experimentalism in the Velvet Underground. Penn details how David Bowie's production on 'Transformer' replaced Cale's experimental drone with Reed's lyrical focus on New York's sexual underground. He shares several personal anecdotes, including taking Lou Reed to see Jonathan Richman perform and forcing Richman to play his song 'Velvet Underground' in front of Reed. Penn discusses the cultural bravery of the album's transgender themes at the time and its complicated modern reception. He delves into specific tracks, arguing that 'Perfect Day' is darker than it seems and praising 'Street Hassle' as Reed's masterpiece. Penn explains Reed's career trajectory after 'Transformer', suggesting the commercial success scared Reed into making the abrasive 'Metal Machine Music' to reclaim credibility, followed by the bleak 'Berlin'. The conversation touches on Reed's sobriety, his sense of humor, and Penn's own drug-free lifestyle, which formed a bond between them. Josh and Penn also briefly discuss other musical heroes like Iggy Pop, David Bowie, and Debbie Harry. The episode concludes with Penn's elevator pitch for the album and promotions for his own work.
