Pickett was an aspiring actor who sang with a band called The Cordials at night while going to auditions during the day. One night, while performing with his band, Pickett did a monologue in imitation of horror movie actor Boris Karloff while performing The Diamonds' "Little Darlin'". The audience loved it and fellow band member Lenny Capizzi encouraged Pickett to do more with the Karloff imitation.
Pickett and Capizzi composed "Monster Mash" and recorded it with Gary S. Paxton, pianist Leon Russell, Johnny MacRae, Rickie Page, and Terry Berg, credited as "The Crypt-Kickers". (Mel Taylor, drummer for The Ventures, is sometimes credited with playing on the record as well, while Russell, who arrived late for the session, appears on the single's instrumental B-side, "Monster Mash Party".) The song was partially inspired by Paxton's earlier novelty hit "Alley Oop", as well as by the Mashed Potato dance craze of the era. A variation on the Mashed Potato was danced to "Monster Mash", in which the footwork was the same but Frankenstein-style monster gestures were made with the arms and hands.
The song is narrated by a mad scientist whose monster, late one evening, rises from a slab to perform a new dance. The dance becomes "the hit of the land" when the scientist throws a party for other monsters. The producers came up with several low-budget but effective sound effects for the recording. For example, the sound of a coffin opening was imitated by a rusty nail being pulled out of a board. The sound of a cauldron bubbling was actually water being bubbled through a straw, and the chains rattling were simply chains being dropped on a tile floor. Pickett also impersonated horror film actor Bela Lugosi as Dracula with the lyric "Whatever happened to my Transylvania Twist?"
The song was re-released several times and appeared in the Billboard charts on three occasions after the original release — December 1962, August 1970 and May 1973. The BBC had banned the record from airplay in 1962 on the grounds that the song was "too morbid". It was re-released in the United Kingdom in 1973, where it peaked at #3 in early October. To celebrate this popular release, Bobby and the Crypt-Kickers toured Dallas and St. Louis around the 1973 Halloween holiday. On this tour, the Crypt-Kickers were composed of Brian Ray (now guitarist with Paul McCartney), drummer Brian Englund, keyboardist Don Chambers, singer Jean Ray, and others. The "Monster Mash" re-entered the British Charts again on November 2, 2008 at #60.
"Monsters' Holiday", a Christmas-themed follow up, was recorded by Pickett and released in December 1962, peaking at #30 on the Billboard chart. The tune was penned by the renowned novelty song composer Paul Harrison. In 1985, with American culture experiencing a growing awareness of rap music, Pickett released "Monster Rap", which describes the mad scientist's frustration at being unable to teach the dancing monster from "Monster Mash" how to talk. The problem is solved when he teaches the monster to rap. A movie musical based on the song starring Pickett was released in 1995. During the 2004 presidential election, Pickett turned the song into a campaign video and retitled it "Monster Slash," with lyrics by Jerry Altman, in which he critiqued President George W. Bush's environmental policies.
In 1989, Brazilian rockabilly band João Penca e Seus Miquinhos Amestrados released an album called "Sucesso do Inconsciente" which featured "O Monstro Macho" (The "macho" monster), a parody on the original song. 
In 1989, Ross Higgins covered the song for the ABC For Kids0-9 series of albums. It appeared on album #7 and was one of the songs from the project to be promoted with a music video.
The 1996 album Test for Echo by the Canadian rock trio Rush includes an instrumental track, "Limbo", which contains several samples from "Monster Mash" including the line "Whatever happened to my Transylvania Twist?".
In 1997, the horror punk group The Misfits released a music video of them covering "Monster Mash" live. They also released a studio version as a single in 1999, and recorded a separate version for their 2003 album Project 1950.
In 2010, comedian and actor Nick Wiger appeared on Comedy Death Ray Radio's 77th episode in character as Leo Capizzi, the song's co-writer. He performed a fictitious 'unreleased' version of the song that was his original idea for the song, entitled "The Monster Fuck," which graphically depicts sex acts performed by the characters in the song. Wiger returned for two subsequent Halloween episodes - the 252nd and 319th, respectively - in character as Capizzi. During these episodes, he performed "The Monster Fuck, Part 2" and "The Monster Fuck, Part 3: Spooky Orgy," respectively. The songs are identical to "The Monster Fuck," save for alluding to being the second or third part of the song in the chorus.
The Misfits recorded their version of "Monster Mash" in 1997 in a recording studio in Newark, New Jersey.BassistJerry Only later stated that "The 'Monster Mash' was a no-brainer for the Misfits to cover as a timeless Halloween release. The song was always a childhood favorite of mine." The recording was the first time that Only had performed lead vocals for the band, while then-Misfits lead singer Michale Graves provided backing vocals. On October 18, 1997 a live performance of the song was recorded and broadcast from the studio of the New Jersey-based cable television music show "Power Play", the same studio in which the song was recorded.
The Misfits' version of "Monster Mash" was used in a cross-promotion campaign arranged by Deluxo and John Cafiero, who had directed the Misfits' music videos for "American Psycho" and "Dig Up Her Bones", to create awareness of a home video release of the 1967 Rankin/Bassstop motion film Mad Monster Party. Deluxo had recently acquired the rights to the film in hopes of restoring it, but could not find a quality print. They eventually found a quality 16 mm print and the Misfits hosted a special screening of the film at Anthology Film Archives in New York City, with the "American Psycho" music video as an opening featurette. Notable attendees at the screening included members of the Misfits, Cafiero, Marky Ramone, Jimmy Gestapo of Murphy's Law, and executives from both Geffen Records and Roadrunner Records. Deluxo restored Mad Monster Party from the 16 mm print and re-released it on VHS in limited numbers. A music video for the Misfits' live recording of "Monster Mash" was created interspersing clips from the film with footage from their "Power Play" performance, and was intended to be included as a bonus feature on a forthcoming DVD release. However, due to complications over distribution rights, the DVD was not released and the VHS version was discontinued. A DVD version of the film was eventually released in 2003 by Anchor Bay Entertainment, restored from a different 35 mm print.
As part of the promotional campaign, an image of Boris Karloff as he appears in Mad Monster Party was used under license from his daughter Sarah Karloff in artwork for a 7" vinylsingle of the Misfits' version of "Monster Mash". Percepto Records used the same image of Karloff for the cover of the film's soundtrack album which was released in September 1998. The Misfits single was intended to be released the following month, but was delayed due to lack of time to properly mix the studio recording. Instead the artwork was used in connection with a free MP3 download of the band's live recording of "Monster Mash", available through their website as a "virtual single". The image was used again as cover artwork when the finished single was released physically in October 1999 as the first release of the band's new label Misfits Records.
The Misfits' studio recording of "Monster Mash" was included on their 2001 compilation albumCuts from the Crypt. At the insistence of the band's label Roadrunner Records, the live recording was omitted from the album and only the studio version was used. The Misfits recorded a new version of the song, featuring Cafiero on backing vocals, for their 2003 album Project 1950. By this time the band had a new lineup consisting of Jerry Only (bass guitar and lead vocals), Dez Cadena (guitar and backing vocals), and Marky Ramone (drums). Only called this version of the song "probably the best version we've ever done. I'm really happy with it. We've recorded it several times in the past and this is the hardest hitting version of them all." Ramone commented: "'Monster Mash' always reminded me of Boris Karloff. Our version's a lot faster than the original, which was a slower 4/4 beat. I always liked the way the drums seemed to come in out of nowhere after Igor walked across the room." Cadena, meanwhile, remarked that "If I didn't know any better ['Monster Mash'] could have been written for the Misfits."
Two separate pressings of the Misfits single were released, both issued on 7" vinyl in 1999. The first pressing had the studio version on both sides and consisted of 1,000 copies: 800 on green vinyl, 100 on red, and 100 on gold. It was sold by the band while on tour and also by mail order through their "Fiend Club" fan club and official website. 1,000 promotional CD copies of the studio version were also pressed and used for limited solicitation to radio stations. A second pressing of the vinyl single had the studio version on side A and the live version on side B and consisted of 1,000 copies on glow-in-the-dark vinyl, available exclusively by mail order through the band's website. The single sold out and is no longer in print.