[4][5] For four years, Late Night with Conan O'Brien had done remote segments parodying the Westminster Kennel Club Dog Show.

[4] In 1999, Jordan Schlansky[9][10][11][12][13] and the Triumph entourage crashed the 123rd annual[14] Westminster Kennel Club Dog Show at Madison Square Garden, New York City, and after some video shooting, were later ejected by security guards.

Notable moments include a wedding that took place at the line, and the appearances of Blackwolf the Dragonmaster (Richard Washington),[19][20][21][22] a real-life fantasy gaming fan and the "Unofficial Wizard of New York", and Spock who gave everyone the finger.

Triumph offhandedly mentions having anal sex with Lassie, which causes friction between Space Ghost and Moltar over such topics being brought up on television.

[27] The following day, Triumph appeared on Late Night with Conan O'Brien, and gave a press conference about the incident while wearing a neck brace.

During the Democratic National Convention in Boston (from which he was ejected), Triumph and Michael Moore attempted to crash Bill O'Reilly's set.

O'Reilly, having his makeup applied at the time, shouted, "If I have to come out there, Insult Dog, you're gonna be talking a lot higher than you are now.

"[episode needed] He also gained entry to the Republican convention in New York, and even debated actor Ron Silver during the wrap-up on MSNBC.

[34] In October 2008, Triumph made an appearance at Hofstra University in Hempstead, New York during the final presidential debate between John McCain and Barack Obama.

[40] In June 2022, Smigel and six staffers from The Late Show with Stephen Colbert were arrested by the United States Capitol Police for an alleged unlawful entry in the Longworth House Office Building while filming a segment with Triumph during the January 6 attack hearings.

[41] In October 2024, Smigel appeared in the background of multiple crowd shots during the vice-presidential debate between Tim Walz and JD Vance.

[44] In 1999, after Triumph accused Pets.com's sock puppet mascot of being a "rip-off" of Triumph on television shows, in print media, online, and in a letter, the company sent lawsuit threats and cease and desist letters to Smigel claiming "unfair competition, dilution and potentially tortious interference with contract in violation of federal and state laws" and the following year filed a lawsuit against Late Night and Smigel.

Appearing with Triumph on the album and the DVD were singer-actor Jack Black, comic actor Adam Sandler, Saturday Night Live cast members Maya Rudolph and Horatio Sanz; Blackwolf the Dragonmaster from the Star Wars skit; and Conan O'Brien.