Jupiter and Pluto are planets of extremes. Jupiter is the biggest gas giant planet and Pluto is the smallest icy dwarf planet. Even their namesakes span the limits of mythology from god of the sky (Jupiter/Jove) to ruler of the underworld (Pluto/Hades). NASA’s two most recent missions to the outer solar system are New Horizons (Jupiter/Pluto) and Juno (Jupiter). New Horizons flew by Jupiter nearly 10 years ago and flew past Pluto in the summer of 2015, returning fantastic images of this diminutive icy world. Juno went into a polar orbit around Jupiter just this past summer and is currently executing a series of 53-day orbits. Juno is measuring thermal emissions from Jupiter, giving scientists insight into its internal structure and providing the highest resolution images ever of the aurora. We will discuss some of the fascinating discoveries and the very latest results from these missions, ranging from Pluto’s ice mountains that are as big as the Alaska Range to Jupiter’s dynamic and multi-faceted aurorae.