In the US alone, the liquor market with sales in 2020 at $31.2 billion. So it makes sense that celebrities have ventured into the category, particularly those whose music is such a big part of nightlife and are able to advertise their brands on songs that permeate the clubs.

Hip-hop artists didn’t always have their own liquor brands to promote, hence why you would hear frequent mentions of Moët, Dom Pérignon, and Cristal on songs. But a major shift happened when a former Cristal staffer spoke disparagingly about hip-hop embracing the brand in 2006. That led Jay-Z to call for a boycott of the company, and he went on to get involved in the liquor business himself, investing in Armand de Brignac (better known as Ace of Spades), which he recently sold 50 percent of to LVMH. He opened up a door for artists like Travis Scott, who recently partnered with Anheuser-Busch to produce his spiked seltzer Cacti, which sold out in multiple locations less than 24 hours after it was released.

Not all of the celebrities in this story own the brands they endorse, and some brands have been more successful than others, but they’ve all represented a particular moment and spoken to hip-hop’s ability to sell products and make brands relevant. Here, we outlined the 13 most famous celebrity alcohol brands.