Jensen Ackles singing Simple Man first part [JIBcon 2016]

Jensen sings at Asylum 14

Jensen Singing Fair, Brother and Free Falling Honcon 2017

JIB Con 7 - Closing Ceremony

Over 40 minutes of Jensen Ackles singing

J2 Tough Mudder Story

JIB 8 - Jensen Ackles sings "Simple Man" and "Brother

Jailbreak ~ Tennessee Whiskey and Wagon Wheel

Jensen Ackles - Simple Man

Jensen Ackles singing at Jail Break in Rome JIBCon 6 (two songs)

Jailbreak 2016 - "The Weight"

Jensen Ackles Singing for an Hour and 6 minutes

JIB Con 7 - J2 Panel - Part 2 - Proud moments

Jason Manns and Jensen Ackles singing Crazy Love at Asylum 14

Jensen Ackles singing She Talks To Angels - JIB13

2019 JIB10 Orion concert (with improved audio)

JENSEN ACKLES sings Heaven | VANCON 2019

2016 JIBcon Jailbreak - Jensen, Jason, Rob, Tim, Laura, Richard part 2

TorCon 2014 - Ending of J2 Panel (Jensen Ackles being adorable)

Jensen Ackles ''Simple Man'

#JAXCON ~ Jared Padalecki Raps & Jensen Ackles Sings