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One look at Chuckles and you wouldn't have given a thought he was an undercover agent. Most undercover specialists try not to stand out too much, their interaction with the enemy is often limited, most of their efforts are concentrated on the source for information, and they don't wear loud Hawaiian shirts. With his burly figure, Chuckles already stands out from the crowd. He has a gregarious personality that makes him the life of the party, quick-witted and possesses a natural likeability. He is very conscientious of his work that he'll volunteer for dangerous missions just to keep up his cover.
He has shifted from one undercover assignment to another for so many times, no one is sure who he works for anymore. He started as an investigator at the South-eastern Insurance Group in Fort Lauderdale. He still feels a debt of allegiance there. He eventually made his way to the US Army's Criminal Investigations Division.
A Real American Hero continuity
Marvel Comics continuity
Chuckles made his first appearance in issue #60, alongside Fast Draw, Falcon, Law & Order, Zanzibar, and Monkeywrench. The aforementioned Joes become involved with a criminal element inside the U.S. military, who were planning to launch a stolen missile at Cobra Island. Falcon, Fast Draw, and Law believed themselves to be part of the G.I. Joe team, and that this was their first assignment, until Chuckles, who was already conducting an investigation in to the matter, contacted them and revealed otherwise.
In order to address both the missile, the extremists, and the fraudulent use of the G.I. Joe name, Chuckles instructs Falcon and Law to intercept General Hawk at a New Jersey airport. When the plot was revealed to Hawk, he decides to assist them in exposing the plot, but the extremist faction discovers that Chuckles has uncovered the plot. In response to this, the missile is activated remotely, and a battle ensues between Hawk's team and the Dreadnoks, who are both attempting to stop the launch, but fail to realize this. In the end, a Cobra chopper destroys the missile, the plot fails, and Chuckles exposes the extremists and demands their resignations.
After this incident, Chuckles, Law, Order, Fast Draw, and Falcon were formally admitted to the G.I. Joe team
Chuckles went on to take part in a number of missions, including a raid on the Cobra Consulate building in New York.
Devil's Due Comics continuity
Chuckles also appeared in the Devil's Due Publishing series G.I.Joe Declassified #1 written by Larry Hama. The 3-issue series acted as a prequel to Marvel's ARAH, however In 2009, IDW Publishing took over the license for G.I. Joe comics, and started a new series that continues where the Marvel Comics series ended. The series began with a free comic book day issue #155 ½, and replaces all of the Devil's Due Publishing continuity that was established. This series is again written by Larry Hama. In his short appearance a younger Chuckles simply referred to as Special Agent Provost (or Mr. Ha Ha, he jokingly declares), indicating he worked for the F.B.I. prior to joining the Joes.
In the scene he meets with Hawk (along with Clutch and Breaker acting as escorts) at the War Memorials located on Manhattan Island's Battery Park. He handed Hawk a blurry picture taken of a helicopter pilot in unknown fatigues located in Sierra Gordo (a Cobra pilot). This story took place shortly after the G.I. Joe unit was formed and before Cobra declared itself openly. He also helps to relate a story he was witnessed to that led to Hawk's court martial case.
Action Force (British) Comics continuity
Hasbro Comics continuity
Sunbow animated series
Chuckles was among the new recruits introduced in G.I. Joe: The Movie, nicknamed The Rawhides. He was introduced alongside Falcon, Jinx, Tunnel Rat, Big Lob, and Law and Order. His depiction here is quite different from that of the comic, as he has no lines in the film and may be mute. He is also shown to have considerable physical strength, able to bare-handedly dislodge a missile from a HAVOC, hold it over his head, run with it at full speed, and toss it a considerable distance.