Limp Bizkit – ‘Rollin’ (Air Raid Vehicle)’ (2000)

A personal favourite on this list, it does not get any weirder than the unprecedented sensation of Limp Bizkit. The new millennium was largely dominated by Fred Durst’s renditions of nu-metal: rap-metal that spoke to a generation clouded with dissatisfaction, apathy and angst. Yet, in the case of ‘Rollin’, they offered a strangely motivational call to “Breathe in, now breathe out… Keep rollin’”, combined with their usual “Don’t fuck with us” attitude, of course. With ‘Rollin’, Limp Bizkit reached number one on the UK singles chart, seeing the band achieve their biggest international hit.

Limp Bizkit have always been unapologetically goofy: just look at their name, or the title of the album from which ‘Rollin’ came, Chocolate Starfish and the Hot Dog Flavored Water. Humorous and undeniably weird, they never took themselves seriously and made this obvious, which was what remained so shocking about how much of a phenomenon they were.

Why not lean into semi-absurdity and write a song with all of the elements for an inevitable hit of hip-hop melodies combined with inventive metal riffs from Wes Borland, and a repetitive mantra for a chorus that even the most reluctant person cannot help but sing-along to?

The Beatles – ‘Yellow Submarine’ (1966)

While ‘I Am the Walrus’ may claim the title as The Beatles’ weirdest single, ‘Yellow Submarine’ was the one to earn a number one spot upon its release in 1966, reaching the top of the charts in the UK and several other countries across Europe, Australia, Canada and New Zealand. The song also won an Ivor Novello Award that year, for having the highest certified sales of any single written by a British songwriter and issued in the UK.

As Paul McCartney has explained, the central idea was to write a children’s song, imagining a happy place brought to life with fantastical melodies and images of the “sky of blue and sea of green” that they live beneath, surrounded by friends. Sweet and simple, ‘Yellow Submarine’ sounds fit for a children’s television programme, in the best of ways, finding space within the psychedelia of the decade that blurred the lines between fantasy and reality.

Herman’s Hermits – ‘I’m Henry VIII, I Am’ (1965)

The shortest song on this list, and considered one of the shortest songs to ever reach the top of the Billboard singles chart at just one minute and 50 seconds, ‘I’m Henry VIII, I Am’ was Herman’s Hermits’ second US number one. The song itself dates back to 1910, a British music hall tune meant for theatrics and entertainment. Its chorus tells the story of Henry, whose wife has been married seven times previously, all to different Henrys.

When Herman’s Hermits offered their rendition in 1965, it was named “the fastest-selling song in history” at the time, even taking The Rolling Stones’ ‘(I Can’t Get No) Satisfaction’ off its pedestal. Surprisingly, the song was not issued in the UK until two months later, when it was included on the band’s self-titled UK debut album for EMI.

Prince – ‘Batdance’ (1989)

Prince recorded ‘Batdance’ for the soundtrack of Tim Burton’s 1989 adaptation of Batman, and the musician placed multiple projects on hold in order to produce nine tracks for the film.

The song harnesses the chaos of the comic book characters, bringing its weirdness to new heights. It opens with samples of Jack Nicholson’s Joker, his sinister laugh, maniacal plots and schemes, while the cartoonish echo of “Batman!” fills in between verses. Guitar notes couple with futuristic-sounding synth beats and piano medleys, crafting a dance rhythm all the way through that brings Prince’s signature sound into the mix. 

Still, where elements of classic Prince formed the basis of the tune, the song was nonetheless considered “weird”, certainly unexpected, considering where Prince’s discography had travelled, thus far. Nonetheless, ‘Batdance’ was a hit, reaching number one on the Billboard Hot 100 and earning Prince his first number one since ‘Kiss’ three years earlier.

Chuck Berry – ‘My Ding-a-Ling’ (1972)

Chuck Berry was certainly nicknamed the ‘Father of Rock ‘n’ Roll’ for a reason, defining the blend of rhythm and blues with guitars that permanently defined the rock genre’s sound. His legacy, however indistinguishable from music history, remains complex, tainted by a number of controversies and improper conduct. Where Berry’s immoral behaviours overshadowed his talents, he continued to be revered for the latter, but in a weird twist of its own, he only achieved one number one single: the unfortunate ‘My Ding-a-Ling’.

The song is a novelty one, originally written and recorded by Dave Bartholomew in 1952, and later covered by Berry in 1972. Surprisingly, it would be his only chart-topper on the Billboard Hot 100, and it is possibly the strangest on this list.

As its title suggests, the lyrics are primarily filled with double entendre, and many radio stations refused to play the song. Frankly, it is an absurd and barely listenable song that, somehow, perhaps as a result of sheer shock, more than anything else, managed to be a whirlwind hit.