FAQ: When I press Play now on an artist page how does Roon choose the songs to play?
When you press Play now on an artist's page Roon randomly shuffles and plays from that artist's discography, as well as any tracks they are featured on.
You can also use the down arrow next to the Play now button to chose other quick play options, such as Start radio. Start radio will play random selections by the artist, as well as similar music by their contemporaries and collaborators. Radio selections are shaped by your listening history as well as those of other subscribers who share your taste in music.
Bonus tip: the quick play options on an artist page can be customized by going to Settings>Play actions>Composers and artists>Edit.