We give a precise functional comparison between classical and free convolutions. If $μ$ and $ν$ are compactly supported probability measures, we show that the expectation of $f$ over the classical convolution $μ* ν$ is at least the expectation of $f$ over the free convolution $μ\boxplus ν$, as long as the fourth derivative of $f$ is non-negative. Conversely, the non-negativity of the fourth derivative is necessary for such a comparison. This comparison is based on the positivity of a related measure on $\mathbb{R}^{2}$, which we dub the convolution comparison measure. We give an expression for this measure using a curious identity involving Hermitian matrices.