Cummings was born in Youngstown, Ohio, and later moved to New Orleans where he worked on Mardi Gras floats and as a door-to-door salesman. He then moved to California, where he worked odd jobs before he got into voice acting. He is known for his ability to mimic Sterling Holloway's high voice.
In other work outside of Disney, he voiced Steele, the main antagonist of Balto, Cat in the Nickelodeon series CatDog, Dr. Robotnik in the SatAM version of Sonic the Hedgehog, Fuzzy Lumpkins in the Cartoon Network series The Powerpuff Girls, Vexx in the Ben 10 franchise, provided additional voices for the stop-motion sketch comedy series Robot Chicken, and voiced Malefor in Season 2 of Skylanders Academy, a role that Mark Hamill originated in The Legend of Spyro: Dawn of the Dragon. He is also well-known for being the current voice of Tony the Tiger in the Kellogg's Frosted Flakes commercials.
- Cummings is the third person to voice Winnie the Pooh and Kaa, after Sterling Holloway and Hal Smith.
- He is not related to his fellow voice actors Brian Cummings or Todd Cummings.
- He will reprise his role as Winnie the Pooh in the upcoming live action film. This makes him the second actor to reprise his animated role in a live-action film, the first being James Earl Jones as Mufasa in the 2019 live-action remake of The Lion King.