This article reports experimental insights into the physics of water entry of hydrophobic spheres. In the set of experiments, parameters such as sphere density, diameter, and impact velocity are varied. The trajectory of the sphere after impact, the dynamics of trapped air-cavity, including the cavity formation, and the retraction analysis are given. Furthermore, analysis of the Worthington-jet, the cavity ripple, and early bubble shedding after the air-cavity detachment is carried out. At the location of cavity closure, radial expansion and contraction behavior are reported for the case of the shallow seal (near the air-water interface), while for the deep seal, only one such behavior is observed. Further, five cavity shapes are recorded based on the cavity retraction behavior (i.e., shallow, deep seal), namely, conical shape, slender-cone shape, telescopic shape, spearhead shape, and the thick spearhead shape. The radial dynamics and radial surface energy analysis are reported at various locations on these cavity shapes to find that the thick spearhead cavities hold the most cross-sectional surface energy. The slender-cone shaped cavity generates the fastest Worthington-jet, followed by the telescopic shaped cavities. The thick spearhead shaped cavities are reported to have the longest intact Worthington-jets, followed by the spearhead shaped cavities. Finally, a new regime map is presented for single ripple and multiple ripple behaviors at the time of retraction in the wake of descending spheres. A bubble shedding behavior has also been characterized as the most frequent bubble shedding for shallow seal and associated longer bubble length compared to the other cases.