Jim Cummings' foray into voice-over was an interesting series of events. As a teenager, he moved to New Orleans where he worked as a deckhand and designed/painted Mardi Gras floats. He was also a drummer for a rock band called Fusion. He later relocated to California where he started a family and managed a video store during the 80s'. In 1984, he scored his first voice-over gig as Lionel on Disney's Dumbo's Circus. From there his career took off and according to his IMDb, he currently has over 500 voice credits to his name.

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Cummings has acted on several different networks and studios but he's mostly worked with Disney. Some of his famous roles being Razoul, Tigger, and Darkwing Duck. His more recent works include shows on Cartoon Network and even a feature-length animated film from a few years back. Without further delay, here are Jim Cummings' 10 best roles so far, ranked.

10 Lord Boxman (OK K.O.! Let's Be Heroes, 2017-2019)

Lord Boxman was the proprietor of Boxcorp, a company that manufactured robots. He used these robots to attack the plaza however, he was usually foiled by KO and his co-workers/friends Enid and Rad.

Despite his diabolical nature, the plaza workers and other villains didn't take him seriously due to his bumbling nature and incompetence. Fans admired Boxman for his humor, the way he treated his robots as his children and his relationship with Professor Venomous.

9 Don Karnage (TaleSpin, 1990-1991)

Karnage was the notorious leader of the Air Pilots. He and his cronies regularly encountered Baloo and his pals and attempted to thwart them. His wit was only outmatched by his narcissism, which usually led to his downfall. A worthy adversary, Karnage came close to disposing of Baloo on several occasions.

Cummings based Karnage's voice on I Love Lucy actor Desi Arnaz and The King and I actor Yul Brenner. He has since gone on to say that Karnage was a character he enjoyed playing and improvised a lot while portraying him.

8 Monterrey Jack (Chip 'n Dale: Rescue Rangers, 1989-1990)

Jack was a member of the Rescue Rangers and a close friend of Gadget's father. While fun-loving, he was one of the more responsible and level-headed members of the group. Jack was best remembered for his love of cheese and long-winded stories.

Originally, Peter Cullen voice Monterey but Cummings took over from season two and beyond.

7  Ray the Firefly (The Princess & the Frog, 2009)

Born and bred in the Bayou, Ray was an optimistic and hopelessly romantic firefly who guided Tiana and her friends to Mama Odie. Throughout The Princess and the Frog, Ray encouraged Tiana to follow her heart just as he did with Evangeline, the North Star.

Cummings pulled off an authentic Cajun accent which he owed to his experience as a deckhand in New Orleans. Fans were taken saddened by Ray's death but were happy to see he ended up with Evangeline as a star. Ray's one of Cummings' favorite characters.

6 Dr. Robotnik (Sonic the Hedgehog, 1993-1994)

The main antagonist of the series and the Sonic franchise as a whole, Robotnik was a devious, supergenius, and warlord who was determined to rule Morbius but was distracted by his countless and futile efforts to destroy Sonic.

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Robotnik utilized the Swatbots to do his bidding along with his nephew Snively. Fans were mesmerized by how sinister and diabolical he was. Robotnik was willing to do anything to achieve his goals even leaving his nephew for dead.

5 The Tasmanian Devil AKA Taz

While the Tasmanian Devil's been voiced by several actors, Cummings has notably voiced him the most. Cummings first voiced the tornado of terror in Taz-Mania! and would reprise the role in several succeeding projects. Being one of the most iconic characters on the Looney Tunes roster, fans have frequently requested Cummings to perform his voice at conventions.

What's even more impressive is that Cummings could be the only Taz voice actor to receive the blessing of none other than Mel Blanc, the original voice of most of the Looney Tunes gang, including Taz. Mel Blanc was one of the first people who heard Jim's demo tape he initially made in the '80s and gave his blessing.

4 Tigger

The rambunctious and ever-bouncing friend of Winnie the Pooh. Cummings continued the role of Tigger from his original voice actor Paul Winchell in The New Adventures of Winnie the Pooh. While their voices were close,  Cummings' Tigger was in his words, "a little more gruff with a little more gravel and sand in there."

Since then, Cummings has been the principal voice of Tigger and considered it a huge honor to carry on Winchell's legacy. Likewise, fans who grew up with Winnie the Pooh held Tigger dear to their hearts.

3 Pete

Pete was initially Mickey's archnemesis but when Goof Troop premiered he became Goofy's neighbor/frenemy. Loud, obnoxious, and bratty, Pete usually looked out for himself and had little regard for anyone else's feelings.

However, he did have a soft spot for his family and occasionally warmed up to Goofy. Since then, Cummings has portrayed Pete in several projects including; A Goofy Movie, House of Mouse, Kingdom Hearts series, and more.

2 Darkwing Duck (Darkwing Duck & Ducktales)

Darkwing Duck animated series

The terror that flaps in the night, Darkwing Duck was on-air for three seasons before ending in 1995. Recently, the character has made a reappearance on the Ducktales reboot. Cummings portrayed Darkwing's TV actor who later assumed the identity of the nefarious Negaduck (another role he initially voiced on the series).

Drake Mallard a.k.a. Darkwing was a self-absorbed but courageous vigilante who fought foes such as Megavolt and Steelbeak. He also has a daughter named Gosalyn, who also served as his sidekick.

1 Winnie the Pooh

The iconic dim and honey-loving Pooh Bear has been voiced by Cummings for over thirty years. Similar to Tigger, Cummings' first gig as Winnie was in The New Adventures of Winnie the Pooh. Having read the books as a kid and owned a stuffed Pooh bear he was honored to play the role.

Cummings' described Pooh's voice as "being at the bottom oh my falsetto, on top of my tenor." Winnie's a character that's dear to Cummings. Having talked to sick children in-character and being moved by the conversations.

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