Brown Dwarfs are objects with masses that straddle “planet” and star classifications. They are defined by an inability to sustain stable Hydrogen burning. Their spectral energy distributions morph with time as they cool from objects as hot as stars to those as cool as Jupiter. The atmospheres of brown dwarfs contain a potpourri of molecules and exotic condensate cloud materials that are extremely relevant to planetary science investigations (both solar system and objects discovered beyond the Sun). In this talk I will discuss the importance of brown dwarfs in the context of how and where they overlap with exoplanet studies. I will particularly focus on brown dwarfs that challenge our understanding of the line between a companion planet and an isolated object. Specifically on the collection of brown dwarfs dubbed “Super Jupiters” that have masses, temperatures, and atmosphere features nearly identical to what is seen or what is expected in exoplanet studies. I will show how Gaia parallaxes paired with long term ground based parallax surveys reveal a diversity in the fundamental properties of brown dwarfs that must be taken into account when considering hot Jupiter and directly imaged exoplanet studies in the JWST era.