We announce the discovery of KELT-16b, a highly irradiated, ultra-short period hot Jupiter transiting the relatively bright ($V = 11.7$) star TYC 2688-1839-1. A global analysis of the system shows KELT-16 to be an F7V star with $T_textrm{eff} = 6236pm54$ K, $log{g_star} = 4.253_{-0.036}^{+0.031}$, [Fe/H] = -0.002$_{-0.085}^{+0.086}$, $M_star = 1.211_{-0.046}^{+0.043} M_odot$, and $R_star = 1.360_{-0.053}^{+0.064} R_odot$. The planet is a relatively high mass inflated gas giant with $M_textrm{P} = 2.75_{-0.15}^{+0.16} M_textrm{J}$, $R_textrm{P} = 1.415_{-0.067}^{+0.084} R_textrm{J}$, density $rho_textrm{P} = 1.20pm0.18$ g cm$^{-3}$, surface gravity $log{g_textrm{P}} = 3.530_{-0.049}^{+0.042}$, and $T_textrm{eq} = 2453_{-47}^{+55}$ K. The best-fitting linear ephemeris is $T_textrm{C} = 2457247.24791pm0.00019$ BJD$_{tdb}$ and $P = 0.9689951 pm 0.0000024$ d. KELT-16b joins WASP-18b, -19b, -43b, -103b, and HATS-18b as the only giant transiting planets with $P < 1$ day. Its ultra-short period and high irradiation make it a benchmark target for atmospheric studies by HST, Spitzer, and eventually JWST. For example, as a hotter, higher mass analog of WASP-43b, KELT-16b may feature an atmospheric temperature-pressure inversion and day-to-night temperature swing extreme enough for TiO to rain out at the terminator. KELT-16b could also join WASP-43b in extending tests of the observed mass-metallicity relation of the Solar System gas giants to higher masses. KELT-16b currently orbits at a mere $sim$ 1.7 Roche radii from its host star, and could be tidally disrupted in as little as a few $times 10^{5}$ years (for a stellar tidal quality factor of $Q_* = 10^5$). Finally, the likely existence of a widely separated bound stellar companion in the KELT-16 system makes it possible that Kozai-Lidov oscillations played a role in driving KELT-16b inward to its current precarious orbit.