Country music star Keith Urban recently performed an intimate, private set at Australian billionaire Anthony Pratt’s holiday party, held at President Trump’s Mar-a-Lago resort. The performance, featuring Urban and a small backing band, included a diverse selection of songs, notably his unique renditions of Chappell Roan’s “Pink Pony Club” and Bob Marley & The Wailers’ “Is This Love?”, alongside his 2024 stand-alone single “Messed Up as Me,” which peaked at No. 12 on Billboard’s Country Airplay chart.

Clips of Urban’s performance were shared on Instagram by realtor Tali Israel, who captioned her post, “President Trump at Anthony Prett’s (who just so generously pledged five billion dollars toward American manufacturing projects) holiday party at the Mar-a-Lago. Amazing people and great entertainment by Keith Urban.” Urban’s representative declined to comment on the private event.

Following the emergence of these videos on social media, many fans expressed confusion and disappointment regarding Urban’s decision to perform at the event. Butch Walker, the current lead guitarist for Train, publicly voiced his displeasure, remarking, “What. A. F—ing. Disappointment.” Conversely, some fans offered a different perspective, suggesting that Urban’s choice to perform songs like “Pink Pony Club” at such an event might have been a deliberate “gag” or an intentional statement.

Urban has historically maintained a nuanced stance on his political affiliations, often playing coy regarding his support in U.S. presidential elections. In a previous interview, he stated, “I’m often amazed that people don’t look to artists’ work — they’re pretty clear on who they are and their views, and I’m no different. … I play to extremely diverse audiences in every way, politically and pronoun, age groups, ethnicity,” suggesting his work itself conveys his perspective. Back in 2017, when questioned about performing at the White House, Urban indicated he would address such an invitation when it arose, emphasizing his desire to “do what’s right” as a citizen.

The inclusion of “Pink Pony Club” in his set is particularly noteworthy, given its association with Chappell Roan, a prominent critic of President Trump. Roan, who performed a special version of the song with Elton John at an Oscars afterparty in March, has openly expressed strong anti-Trump sentiments, while also criticizing elements within the Democratic party for failing marginalized communities. Neither Roan nor the Marley estate has yet commented on Urban's performance of their respective songs.

This performance also follows a significant personal development for Urban, occurring just two months after his separation from actress Nicole Kidman, with whom he had been married for 19 years. Pratt Industries, the company led by Anthony Pratt, is a leading privately owned recycled paper and packaging enterprise. Notably, last year’s Mar-a-Lago-set Pratt holiday party saw comedian Chris Rock abruptly end his set due to alleged violations of his no-filming policy by guests.