This paper explores three groups of time–frequency distributions: the Cohen’s, affine, and reassigned classes of time–frequency representations (TFRs). This study provides detailed insight into the theory behind the selected TFRs belonging to these classes. Extensive numerical simulations were performed with examples that illustrate the behavior of the analyzed TFR classes in the joint time–frequency domain. The methods were applied both on synthetic and real-life non-stationary signals. The obtained results were assessed with respect to time–frequency concentration (measured by the Rényi entropy), instantaneous frequency (IF) estimation accuracy, cross-term presence in the TFRs, and the computational cost of the TFRs. This study gives valuable insight into the advantages and limitations of the analyzed TFRs and assists in selecting the proper distribution when analyzing given non-stationary signals in the time–frequency domain.