Cummings has frequently worked with the Walt Disney Company and Warner Bros., serving as the official voice of Winnie the Pooh since 1988, Tigger since 1989, the Tasmanian Devil since 1991, and Peg Leg Pete since 1992.

[4] Upon his graduation from high school, Cummings relocated to New Orleans, where he designed and painted Mardi Gras floats, worked as a river boat deck hand, and sang and played drums in the regionally-successful rock band Fusion.

In The Little Mermaid: Ariel's Beginning, Cummings voiced King Triton in place of Kenneth Mars, who was unable to reprise the role due to his struggles with pancreatic cancer.

When actor Jeremy Irons, the voice of Scar in The Lion King, developed vocal problems during the recording of the song "Be Prepared", Cummings replaced him on the remainder of the track.

His most famous role in Rescue Rangers was the villainous Fat Cat, and for TaleSpin, he notably starred as the show's main antagonist, Don Karnage.

He later went on to voice original characters for a variety of the company's theatrical and direct-to-video films, such as Ed the Hyena in The Lion King and Ray the Firefly in The Princess and the Frog.

[10] Other villain roles Cummings notably took on include Sierra the Cearadactylus in The Land Before Time VII: The Stone of Cold Fire, and Doctor Robotnik in the Sonic the Hedgehog animated series that aired from 1993 to 1994.

The series became one of the longest-running American children's programs around, having initially run for nine seasons on PBS Kids before being renewed following the launch of Peacock, the streaming service of NBCUniversal.

[14] His recordings in question were mixed with material by Fred Tatasciore, who was the character's credited voice actor for the film and previously played the part for Looney Tunes Cartoons.

Cummings would later go on to reprise the roles of Fat Cat, Darkwing Duck, and Pete for the Chip 'n Dale: Rescue Rangers film, along with the right arm of Shredder from the 1987 Teenage Mutant Ninja Turtles animated series, and bootleg versions of Pooh and Tigger.

Over a year after the film's release, Cummings reprised the role of King Triton for Lego Disney Princess: The Castle Quest, making his first appearance as the character since Ariel's Beginning.

Months later, Cummings reprised the role of Winnie the Pooh for Disney's Once Upon a Studio to sing a portion of When You Wish Upon a Star, the short in question also featured him as the voice of Baloo from The Jungle Book for a similar purpose.

[19] In a separate interview with Collider, Cummings stated that his favorite characters to play are Winnie the Pooh, Tigger, Ray the Firefly, Drake Mallard/Darkwing Duck, and Hondo Ohnaka.