The core collapse of rapidly rotating massive ∼ 10M stars ("collapsars"), and resulting formation of hyper-accreting black holes, are a leading model for the central engines of long-duration gamma-ray bursts (GRB) and promising sources of r-process nucleosynthesis. Here, we explore the signatures of collapsars from progenitors with extremely massive helium cores 130M above the pair-instability mass gap. While rapid collapse to a black hole likely precludes a prompt explosion in these systems, we demonstrate that disk outflows can generate a large quantity (up to 50M ) of ejecta, comprised of 5 − 10M in r-process elements and ∼ 0.1 − 1M of 56 Ni, expanding at velocities ∼ 0.1 c. Radioactive heating of the disk-wind ejecta powers an optical/infrared transient, with a characteristic luminosity ∼ 10 42 erg s −1 and spectral peak in the near-infrared (due to the high optical/UV opacities of lanthanide elements) similar to kilonovae from neutron star mergers, but with longer durations 1 month. These "super-kilonovae" (superKNe) herald the birth of massive black holes 60M , whichas a result of disk wind mass-loss-can populate the pair-instability mass gap "from above" and could potentially create the binary components of GW190521. SuperKNe could be discovered via wide-field surveys such as those planned with the Roman Space Telescope or via late-time infrared follow-up observations of extremely energetic GRBs. Gravitational waves of frequency ∼ 0.1 − 50 Hz from non-axisymmetric instabilities in self-gravitating massive collapsar disks are potentially detectable by proposed third-generation intermediate and high-frequency observatories at distances up to hundreds of Mpc; in contrast to the "chirp" from binary mergers, the collapsar gravitational-wave signal decreases in frequency as the disk radius grows ("sad trombone").