Here is the full list of all 30 Paint the Town Red achievements.
Defeat The End
Reach Fire & Blood I
Defeat the Trickster
Reach The Construct
Upgrade one of the Beneath classes
Destroy the Jerk
Capture the Pursuer
Defeat the Aberration
Reach Islands I
Defeat the Necromancer
Reach Ruin I
Reach Crystal Caverns I
Unlock a permanent upgrade in Beneath
Defeat a Shard Lord
Rescue the Apostate
Complete the Pirate Cove in Challenge mode
Complete the Disco in Challenge mode
Complete 5 Arena challenges
Complete 3 Arena challenges
Complete the Prison in Challenge mode
Complete the Prison in Challenge mode in under 2:30 minutes
Complete the Biker Bar in Challenge mode in under 3:30
Complete an Arena challenge
Complete Arena Challenge 1 in under 9:30 minutes
Complete the Biker Bar in Challenge mode
Complete a Scenario level without modifiers
Die for the first time in Beneath
Enter Beneath for the first time
Complete the Western Saloon in Challenge mode
Complete the Saloon in Challenge mode in under 3:30 minutes