This study performed mechanical tests and monitored acoustic emissions (AE) in shale samples with six bedding layer orientations (β = 0°, 30°, 60°, 90°, 120°, and 150°) to investigate the progressive damage mechanisms under direct shear. The results revealed that the peak shear load (Pcr), crack initiation threshold (Pci), crack damage threshold (Pcd), and cumulative AE count exhibited an approximate M-shaped trend as the bedding angle increased. The Pci, Pcd, and Pcr values were minimal for shale specimens with β = 0°, Pcd and Pcr were maximal at β = 150° (followed by β = 60°), and Pci reached the maximum at β = 60°. Thus, shale exhibits complex and asymmetric mechanical behavior under direct shear, a phenomenon seldom documented. The three-dimensional spatiotemporal evolution of the AE, evolution of b-values, peak frequency distribution, and the rise angle-average frequency (RA-AF) indicated that the microscale mechanism governing the asymmetric progressive failure of anisotropic shale under direct shear involved significant asymmetry in the formation type and scales of cracks. The AE characteristics of anisotropic shale were analyzed using multifractal theory. The width of the multifractal spectrum, Δθ, accurately reflected the anisotropic characteristics of the AE time series. Moreover, the variation in the fractal dimension, Δf, indicated that the different probabilities of microcracks with high AE energy are the fundamental cause of the shale's asymmetric failure.