Coolio

Artis Leon Ivey Jr. (August 1, 1963 – September 28, 2022), known professionally as Coolio, was an American rapper, record producer, and actor. Coolio achieved mainstream success in the mid-to-late 1990s with his albums It Takes a Thief (1994), Gangsta's Paradise (1995), and My Soul (1997). He was best known for his 1995 Grammy Award-winning hit single "Gangsta's Paradise", as well as other singles "Fantastic Voyage" (1994), "1, 2, 3, 4 (Sumpin' New)" (1996), and "C U When U Get There" (1997). Description above from the Wikipedia article Coolio, licensed under CC-BY-SA, full list of contributors on Wikipedia.
Cast

Get Over It
Coolio

Shriek If You Know What I Did Last Friday the Thirteenth
Principal

Dracula 3000
187

Red Water
Ice

The Convent
Officer Starkey

Exposed
Big Heat

Pterodactyl
Capt. Bergen

Air Force Z
Veep

China Strike Force
Coolio

Stupidity
Self

Outlawz: Worldwide
Self

Storm Watch
Outlaw
Celebrity Mix
Self (archive footage)

Stealing Candy
Brad Vorman

The Beat
Emcee

A Wonderful Night in Split
Franky

An Alan Smithee Film: Burn, Hollywood, Burn
Dion Brothers

Judgment Day
Luther / 'Lucifer'

Gangland
Officer Harris

Submerged
Jeff Cort
Media Whore
Self

Two Hundred Thousand Dirty
Manny

Grad Night
Michael Adkins

Mayday Z
Coolio

The Goddamn Comedy Jam
Self

Bad Trip
Tyrone / Jerome / Cherone

Daredevil
Dante Jackson (Director's Cut)

It Wants Blood 2
Don Luscious

Phat Beach
Coolio

Bobcat Moretti
Coolio

In Pursuit
Carl Wright

Three Days to Vegas
The Flow

Dear God
Gerard

On the Line
Lt. Gil Suggs

Leprechaun in the Hood
Self (uncredited)

Batman & Robin
Banker

Railroad to Hell: A Chinaman's Chance
Roger

Futurama: Bender's Big Score
Kwanzaa-bot (voice)

Tapped Out
Cool

Gang Warz
Dunzio Day

The Orange Years: The Nickelodeon Story
Self

Perfume
T

Lord of the Freaks
Self

United Skates
Self

Dope Case Pending
Unknown