From Oldest to Newest:
Grim (Usual name, also goes by Barry)
Very Barry Christmas (Christmas)
Grim Quagmire (Simp gimmick)
Pepe le Quagmire (See above)
Char Aznable (Mobile Suit Gundam)
Grim Kimura (RIP Hana Kimura)
Grimhail Gorbachev (Communist name)
Grim Fandango (the video game)
Grim Cornette (Corny)
Tuco Grimirez (Good, Bad, Ugly reference)
The Grimch (Christmas again)
Grimmie Lee (RIP Brodie Lee)
Grimus Augustus (Roma Gloria)
Judge Barry
Grimnight Express (RIP Bobby Eaton)
Grim Reaper (Halloween name, also a callback to my name back in 2013)
Royal Reaper (Royal Rumble)
Grim Theft Auto (Current)