We report on our early photometric and spectroscopic observations of the extremely luminous Type II supernova (SN) 2008es. SN 2008es, with an observed peak optical magnitude of m$_V$ = 17.8 and at a redshift z = 0.213, has a peak absolute magnitude of M$_V$ = -22.3, making it the second most luminous SN ever observed. The photometric evolution of SN 2008es exhibits a fast decline rate (åisebox-0.5ex 0.042 mag d$^-1$), similar to the extremely luminous Type II-Linear (II-L) SN 2005ap. We show that SN 2008es spectroscopically resembles the luminous Type II-L SN 1979C. Although the spectra of SN 2008es lack the narrow and intermediate-width line emission typically associated with the interaction of an SN with the circumstellar medium of its progenitor star, we argue that the extreme luminosity of SN 2008es is powered via strong interaction with a dense, optically thick circumstellar medium. The integrated bolometric luminosity of SN 2008es yields a total radiated energy at ultraviolet and optical wavelengths of gsim 10$^51$ erg. Finally, we examine the apparently anomalous rate at which the Texas Supernova Search has discovered rare kinds of SNe, including the five most luminous SNe observed to date, and find that their results are consistent with those of other modern SN searches.