An automatic air release plunger is provided for unclogging an obstructed drain in a plumbing fixture having undrained wastewater. The plunger includes a handle and a hollow, compressible plunger head. The plunger head is coupled to the handle at the plunger head's proximal end. The plunger head also includes a seal extending from its distal end that is capable of sealing the plunger head to a drain opening of the plumbing fixture. Additionally, the handle and plunger head include automatic air release features that allow air to flow along an air-escape path from inside of the hollow plunger head into a void formed in the interior of the handle, and thereafter into a channel which extends from the proximal end of the plunger head to a gap at a proximal end of the handle where the air is released whenever the plunger head is compressed.