Since Penzias and Wilson discovered the cosmic microwave background (CMB) in 1964, observation of CMB has been central to the development of modern and precision cosmology. Combined with other probes, it has told us so many things about the Universe - how the Universe began, how the Universe has evolved, what the universe is made of, and still, how many questions are unsolved about the Universe. Throughout its history, the CMB observation has gone through a unique progression - ground-based telescopes, balloon-borne telescopes, and space missions have helped one another and contributed to scientific advancement in their own ways. I am new to the field compared to the history, and I may be out of my depth, but I will make my attempt to review this history and the nature of the CMB observation to realize the synergy between the observations from the ground and the sky. This leads us to the discussion relevant today: how the CMB observations from the ground and the sky may work together now and in the future. I will review the synergies and complementarity between these different approaches, with a focus on CMB polarization measurements, and conclude with a promising outlook for the field.