A reproducing apparatus includes: a connecting part which is connected to an audio signal output apparatus through the three pole terminal; a storage part which stores content data including first and second channel audio data; a reproducing part which reproduces the content data; a first converting part which converts the first channel audio data included in the content data reproduced by the reproducing part into the first channel audio signal; a second converting part which converts the second channel audio data included in the content data reproduced by the reproducing part into the second channel audio signal; and a measuring part which measures at least any one of an amount of sound leakage in the second output unit caused by outputting the first channel audio signal and an amount of sound leakage in the first output unit caused by outputting the second channel audio signal.