Abstract The core collapse of rapidly rotating massive ∼ 10M _⊙ stars (“collapsars”), and the resulting formation of hyperaccreting black holes, comprise a leading model for the central engines of long-duration gamma-ray bursts (GRBs) and promising sources of r-process nucleosynthesis. Here, we explore the signatures of collapsars from progenitors with helium cores ≳ 130M _⊙ above the pair-instability mass gap. While the rapid collapse to a black hole likely precludes prompt explosions 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 ⁵⁶Ni, expanding at velocities ∼0.1 c. Radioactive heating of the disk wind ejecta powers an optical/IR transient, with a characteristic luminosity ∼ 10⁴² erg s⁻¹ and a spectral peak in the near-IR (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 _⊙, which—as 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 IR follow-up observations of extremely energetic GRBs. Multiband gravitational waves of ∼ 0.1–50 Hz from nonaxisymmetric instabilities in self-gravitating massive collapsar disks are potentially detectable by proposed observatories out 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”).