Headphone Jack Trouble

For a while now my sound will randomly stop working when using headphones. This happens on every browser and every program I use, and I have tried various things to fix it like update my audio drivers. Whats weirder is when I'm watching a Youtube video, if the sound stops working and I remove my headphones, the video will stop playing and if I plug my headphones back in after this occurs, it crashes the entire video. I have a video down below demonstrating this.