While most stars in the universe experience relatively serene deaths, a small fraction explode as supernovae, either through the collapse of the core of a massive star or the accretion of matter onto a white dwarf past the point of stability. Supernovae are extremely important in the life cycle of matter in a galaxy throughout all phases of their existence. The progenitor stars can blow strong winds into the surrounding interstellar medium. The neutron-rich environment in the aftermath of the explosion is the creation site for most of the elements on the periodic table. For thousands of years post-explosion, the expanding ejecta from the supernova drive a powerful shock wave over thousands of cubic parsecs of the galaxy, forming a supernova remnant. The details of these various transitions, that is, how a system goes from stellar progenitor to supernova to supernova remnant, are murky. What types of stars lead to what types of supernovae? Do different types of supernovae produce supernova remnants that are different in some way? In this talk, I will examine several specific supernovae and supernova remnants to try to piece together the puzzle. I use a multi-wavelength approach, and show how everything from the dynamics of the shock wave to the abundance of materials in the X-ray emitting ejecta offer clues to these mysteries.