Drake is apparently unhappy with merchandise using the catchphrase YOLO without paying him royalties.
The Canadian rapper uses the phrase, which stands for You Only Live Once, in his hit song The Motto. It is not known if he has trademarked the slogan, but it appears he is not the first person to have coined the phrase.
Drake, 26, posted several pictures on the photo-sharing site Instagram on Christmas Eve, hinting that he wants a share of any merchandise bearing the phrase YOLO, gossip website Gawker.com reported.
The first picture shows a row of shelves with baseball caps in various colours being sold at Walgreen's, which Drake captioned: "Walgreen's... you gotta either chill or cut the cheque."
The second photo shows a blue T-shirt featuring the popular cartoon characters Charlie Brown and Snoopy which reads "YOLO is my motto." Drake wrote: " Macy's... same goes for you."
The acronym YOLO for You Only Live Once is thought to have first been used in 2004 by Adam Mesh on the third season of NBC's reality show Average Joe.
Mesh launched a clothing line bearing the slogan, and recently tweeted to the Huffington Post that he had meant the term as inspiration to live life to the fullest, adding "Disappointed in current use. I have moved on."
In July 2006, the band The Strokes released single You Only Live Once, and launched Operation YOLO asking fans to request the song on the radio.
Drake is first known to have used the phrase in October 2011, when he tweeted "You only live once...YOLO" along with a picture of him standing on a balcony overlooking a city.