Brush and comb polymers, characterized by dense polymeric side chains attached to a backbone polymer chain, exhibit super-softness (elastic modulus < 100 kPa) in the absence of solvent. The dissertation comprised four projects. The first project was "Adhesion and Mechanical Properties of PDMS Bottlebrush Elastomers." This chapter quantified the adhesion properties of PDMS bottlebrush elastomers to glass through a contact adhesion test, comparing them to linear PDMS networks. The critical energy release rates of both materials were calculated as a function of interfacial separation velocity. This work provided insights into the distinctive attributes arising from the molecular architecture of bottlebrush elastomers. The second project was "PDMS Comb Polymers with Adjustable Hydrogen Bonding Interactions." Hydrogen bonding units were attached to the end of side chains, forming physical crosslinks. Rheological properties were measured by varying the density and strength of hydrogen bonding, with a thorough investigation of thermal reversibility to understand the dynamics of hydrogen bonding. This chapter revealed how hydrogen bonding units effectively regulated mechanical properties and promoted self-healing characteristics. The third project was "Puncture Mechanics of PDMS Bottlebrush Elastomers." This chapter explored the puncture mechanics to derive multiple mechanical properties from a single test. Through systematic variation of sample volume and indenter dimensions, the influence of confinement effects on puncture test outcomes was studied. Experiments conducted with confinement-free sample sizes demonstrated consistent results across varying volumes, offering advantages for testing limited-volume samples. Additionally, a comparison of mechanical properties from puncture testing and conventional mechanical tests revealed a reliable correlation. The fourth project was "PDMS Bottlebrush Elastomers with Mobile Crosslinks." This chapter introduced slide ring (SR) crosslinks into bottlebrush elastomers. Transparent elastomers with SR crosslinks were obtained, and their mechanical properties were evaluated and compared to those with conventional fixed crosslinks (FC). While elastomers with SR showed enhanced softness, fracture energy through puncture tests was similar to or less than FC crosslinked material, suggesting ineffective sliding of rings. The limitations of current material systems were discussed. Overall, this dissertation contributed to a deeper understanding of the adhesion and mechanical properties of brush and comb PDMS elastomers. It emphasized the importance of molecular architecture and crosslinking strategies in controlling mechanical properties and provided valuable insights for their design and application in various fields.