What was the most significant moment in the history of Phoebe's music career on Friends?

Phoebe Buffay's music career was one of the most memorable aspects of the hit TV show Friends. Her quirky personality and unique musical style endeared her to fans of the show, and she had several memorable musical moments throughout the series.

Perhaps the most significant moment in Phoebe's music career on Friends was when she performed her song 'Smelly Cat' in Central Perk. The song became an instant fan favorite and was even released as a single, with proceeds going to charity. 'Smelly Cat' became a cultural phenomenon and is still remembered and beloved by fans today.

Other memorable musical moments for Phoebe on Friends include her performances of 'Sticky Shoes,' 'Blackout,' and 'Grandma,' among others. Each of these songs showcased Phoebe's unique musical style and quirky personality, and helped to make her one of the most beloved characters on the show.