The water entry, crown formation, and cavity dynamics of gravity-driven thick solid and annular disks were studied by conducting a series of detailed laboratory experiments. Three different release conditions were examined to study the fully guarded and partially guarded release conditions on the cavity dynamics. The effects of aspect ratio, geometry, and density of disks on crown formation, interface impact, seal development, and air entrainment were investigated. Four crown shapes were identified, and the crown structure was classified based on the dimensionless moment of inertia, I*, and the impact Froude number, Fro. The effects of controlling parameters on variations of crown dimensions were investigated. It was found that the normalized crown diameter decreased with I* and crown geometries were found to be smaller in annular disks. Experimental observations have shown that high-density disks have larger pinch-off depth and form a deep seal in the ambient water. The normalized pinch-off depth increased with Fro and the normalized pinch-off depth in cylindrical thick disks were smaller than thin disks and spherical objects. The temporal variations of cavity indicated a non-linear correlation between the growth rate of normalized pinch-off depth and time. The disk's velocities in three different stages were measured, it was found that the settling velocities followed a linear relationship with I*, and it was affected by the release conditions. The velocity and vortex fields were extracted from the particle image velocimetry data. The velocity fields showed that the solid disks affected a greater surrounding ambient in comparison to the annular disks due to their higher initial momentum. Periodic vortex shedding was formed in the wake of annular disks, and the frequency of the vortex field was found to be proportional to the disk density.