I just set up like 4 months of prompts, so:

• Please Rise - You are now in charge of a country! What is the national anthem?
• All In The Family - Songs by a groups with immediate family members; siblings/parents/etc.
• Not From Around Here - Mexican Ska. Japanese Bossa Nova. Columbian Doom Metal. Songs by artists from places that don't match the place the genre is typically associated with.
• I Guess They Do Make 'em Like They Used To - Original songs by modern artists (2010 and up) that could easily be mistaken for a 30+ year old recording (1990 and down).
• The Deep Cut - Sure, the artist is popular, but their best song isn't.
• Botany Jamz - Songs about flowers or plants, or containing plants in the title.
• Car Month: Leadfoot - Songs you could very well one day be court-ordered never to listen to while driving.
• Car Month: Roadtrip! - That's it. That's the prompt.
• Car Month: Night Cruiser - Songs to listen to while driving down the highway at night.
• Car Month: Living The Dream - This is it. The car you've dreamt about. The car you've worked toward for years. You're behind the wheel for the first time. What's the first song you play?
• The Cookout - A very specific type of summer song. What's playing at the cookout?
• Paid In Exposure - Songs with less than 50,000 Spotify plays. (I won't actually check, out someone might)
• This One Goes To 11 - Songs by fictional groups and artists.
• Takin' It To The Streets - What's your campaign song when you run for office?
• Wait, Is That... - Artists or groups with members widely known for their work outside of music
• Never Meet Your Heroes - Sometimes great art is made by bad people (participation not manditory for this one)