Discriminating quark jets from gluon jets is an important but challenging problem in jet substructure. In this paper, we use
the concept of mutual information to illuminate the physics of quark/gluon tagging. Ideal quark/gluon separation requires
only one bit of truth information, so even if two discriminant variables are largely uncorrelated, they can still share the
same "truth overlap". Mutual information can be used to diagnose such situations, and thus determine which discriminant variables
are redundant and which can be combined to improve performance. Using both parton showers and analytic resummation, we study
a two-parameter family of generalized angularities, which includes familiar infrared and collinear (IRC) safe observables
like thrust and broadening, as well as IRC unsafe variants like p T D and hadron multiplicity. At leading-logarithmic (LL)
order, the bulk of these variables exhibit Casimir scaling, such that their truth overlap is a universal function of the color
factor ratio C A /C F . Only at next-to-leading-logarithmic (NLL) order can one see a difference in quark/gluon performance.
For the IRC safe angularities, we show that the quark/gluon performance can be improved by combining angularities with complementary
angular exponents. Interestingly, LL order, NLL order, Pythia 8, and Herwig++ all exhibit similar correlations between observables,
but there are significant differences in the predicted quark/gluon discrimination power. For the IRC unsafe angularities,
we show that the mutual information can be calculated analytically with the help of a nonperturbative "weighted-energy function",
providing evidence for the complementarity of safe and unsafe observables for quark/gluon discrimination.