City Works performed as part of a "hippie burlesque" at Shanghai Junk, a strip club owned by Chong's family.

As the improv group had not been a financial success at the strip club—they drew a large but low-spending crowd—the two decided to form a comedy duo and play different venues.

[3] The pair performed stand-up shows, released many successful comedy record albums, and starred in a series of low-budget films.

[1] Some of their best-known comedy routines and songs include "Earache My Eye", "Basketball Jones", "Santa Claus and His Old Lady", and "Sister Mary Elephant".

[1] It became something of a cult classic, and was also successful enough at the box office (grossing over $44 million despite a low budget)[4] to warrant two sequels: Cheech and Chong's Next Movie in 1980, and Nice Dreams in 1981.

They also appeared in smaller supporting roles in Graham Chapman's Yellowbeard and Martin Scorsese's After Hours, as well as a Joni Mitchell song ("Twisted" on the album Court and Spark).

[6] In 1997, Chong made an appearance on Marin's TV series Nash Bridges, in an episode titled "Wild Card," which contained a reference to their iconic "Dave" skit from their 1972 debut album.

In a plea bargain which allowed his son and wife to remain out of jail, Chong pleaded guilty to charges of conspiring to distribute drug paraphernalia in May, and in September 2003 was sentenced to nine months in federal prison, fined $20,000, and forced to forfeit $120,000 in assets.

Beginning in September 2008, Cheech and Chong reunited for the Light Up America comedy tour[9] which opened in Ottawa, making a radio program appearance on The Bob & Tom Show.

[12][13] On April 17, 2009, while on the Sydney leg of their "Cheech and Chong Light Up Australia" Tour, they had to delay the start of their show as it became the target of a drug operation by the New South Wales Police.

[19] The pair appeared together on The Late Show with Stephen Colbert on April 23, 2018, in response to recent news that John Boehner had joined the board of a marijuana company.

[21] On April 17, 2024, Cheech & Chong were added to Call of Duty: Warzone & Modern Warfare III as a part of a purchasable bundle worth 3,000 CoD Points (equivalent to 30 USD).

Cheech and Chong's manager thought the script was very funny; however, the comedy duo wanted complete creative control, so Reitman told the screenwriters to rewrite it for Bill Murray and Harold Ramis.

[24] Screenwriter Tom McLoughlin also pitched a sequel to the slasher film Friday the 13th in which Cheech and Chong, playing camp counselors, faced off against killer Jason Voorhees, as a comedy horror movie in the vein of Abbott and Costello Meet Frankenstein.

Due to the duo not getting along with each other at the time, and Whoopi Goldberg taking interest in the role of Shenzi, Chong was not cast, but Cheech played the part of Banzai.