He has also worked occasionally as an actor and starred as Master Chief Petty Officer Carter Holt in the WWE Studios production Behind Enemy Lines: Colombia in 2009.

[17] Anderson, under the ring name "Two Rivers Jack", made his debut on September 11, 1999, at a North American Wrestling Federation event in Whitewater, Wisconsin, losing to Golga.

When he arrived, Jim Cornette was in charge of the organization and, according to Anderson, did not see potential in his abilities and declined to feature him as more than an occasional bit-player on OVW's programming.

[22] When Cornette departed, his replacement, Paul Heyman, showed immediate interest in Anderson, comparing his qualities to The Rock and Stone Cold Steve Austin.

[57] Raw General Manager William Regal, scheduled a match between Kennedy and Carlito, in which the winner would receive an opportunity to face off against Umaga at SummerSlam.

This angle was written because Kennedy being named one of the eleven wrestlers implicated in a steroid scandal and therefore suspended for thirty days in accordance with WWE's Wellness Policy.

[62][63] At Cyber Sunday on October 28, Kennedy and Hardy were two of the eligible wrestlers that could earn a WWE Championship match that evening, pending a fan votes.

[83] At Against All Odds on February 14, Anderson defeated Kurt Angle and Abyss to advance to the finals of the 8 Card Stud Tournament, where he lost to D'Angelo Dinero.

[91] At Slammiversary VIII on June 13, Anderson and Hardy, now known collectively as the Enigmatic Assholes, defeated Beer Money, Inc. (Robert Roode and James Storm) in a tag team match.

[92] At Victory Road on July 11, Anderson and Hardy attempted to win the TNA World Heavyweight Championship from Rob Van Dam in a four-way match, also involving Abyss, but both were unsuccessful.

[93] On the August 19 edition of Impact!, the TNA World Heavyweight Championship was vacated and Anderson was entered into an eight-man tournament for the title, defeating Jay Lethal in the first round[94] and D'Angelo Dinero in the semifinals at No Surrender on September 5.

[105] Eleven days later, Anderson defeated Kurt Angle and Rob Van Dam in a three-way match to earn a rematch for the TNA World Heavyweight Championship.

[108] On April 17 at Lockdown, Anderson failed in his attempt to regain the TNA World Heavyweight Championship from Sting in a three-way steel cage match which also included Van Dam.

[111][112][113] At Slammiversary, Anderson defeated Sting after a low blow from Eric Bischoff and a "Mic Check" to win the TNA World Heavyweight Championship for the second time, turning heel once again.

[122] On the September 8 episode of Impact Wrestling, Anderson challenged Kurt Angle, who won the world title at Hardcore Justice, but the match ended in a disqualification due to interference from Immortal.

[125] On November 13 at Turning Point, Anderson and Abyss defeated Ray and Scott Steiner in a tag team match, ending his year-long storyline with Immortal.

[129] On the following episode of Impact Wrestling, Anderson and Jeff Hardy were defeated by Rob Van Dam in a three-way number one contender's match for the TNA World Heavyweight Championship.

[131] On June 10 at Slammiversary, Anderson defeated Hardy and Rob Van Dam in a three-way match to become the number one contender to the TNA World Heavyweight Championship.

[134] On September 27, Anderson received a shot at the vacant TNA Television Championship, but was defeated by Samoa Joe via submission with the "Coquina Clutch".

[138] Anderson wrestled his return match three days later at Genesis, defeating Samoa Joe after interference from Aces & Eights member Mike Knox.

[140] On June 2 at Slammiversary XI, Anderson, Bischoff, and Wes Brisco were defeated by Jeff Hardy, Magnus, and Samoa Joe in a six-man tag team match.

[143] Anderson defeated Joseph Park in his first BFG series match via pinfall on the June 20 episode of Impact Wrestling to earn seven points in the tournament.

[146] Anderson's participation in the Bound for Glory series ended on the September 5 episode of Impact Wrestling, when he was eliminated from a twenty-point battle royal by Samoa Joe.

Later that night, Anderson turned face by costing Bully Ray his no-disqualification match with Sting and announcing himself as his TNA World Heavyweight Championship opponent at No Surrender.

[169] In his first independent appearance since his firing from TNA, Anderson competed in Preston City Wrestling's Road to Glory tournament, defeating Luther Ward in the first round and losing to Drew Galloway the next day in the quarter-finals.

[171] On April 29, 2017, at Ring of Honor Masters of the Craft, Anderson made a one-time appearance for the company, unsuccessfully challenging for Marty Scurll's ROH World Television Championship.

[173] At the December 16 tapings, Anderson won an eight-man gauntlet match to replace the injured Zane Dawson in the NWA World Television Championship tournament.

[177] Anderson, along with Mickie James and Josh Mathews, represented WWE at the 2008 Republican National Convention in an effort to persuade fans to register to vote in the 2008 US presidential election.

[180][181] In June 2014, Anderson and comedian David Vox Mullen started the Push The Button podcast to cover topics such as religion, sex, and politics.

[188] In an interview on August 18, 2007, Anderson admitted to using steroids when he was performing on the independent wrestling scene, stating that he had quit using them in November 2005 to comply with WWE's Talent Wellness Program, implying that his job in the promotion was worth more than extra muscle mass.