Hard to narrow it down to just 5, I have a playlist of about 3,000 tracks that I put on shuffle to help calm me down :P
Luckily, there are a handful that I occasionally go to deliberately rather than waiting for the RNG to pick them out for me:

"Autumn Voyage" - Ian Taylor (RuneScape)
"No Care" - Daughter (Not to Disappear)
"Run Away" - blink-182 (Nine)
"The Grand Duchy of Jeuno" - Naoshi Mizuta (Final Fantasy XI)
"Ronfaure" - Nobuo Uematsu (Final Fantasy XI)