12 awful songs by great artists, from Michael Jackson to Justin Bieber

When it comes to the most revered or popular musicians, it’s easy to forget that they’re still only human. Even universally respected artists such as Bob Dylan and Bruce Springsteen have their bad days.

So here it is, the worst songs by otherwise brilliant artists.

“Real Man” – Bruce Springsteen (1992)

You’d be forgiven for mistaking this for an Eighties number, but no, the Boss’s most dated-sounding (and worst) song was actually released the same year as innovative records such as Selected Ambient Works by Aphex Twin, and Dr Dre’s The Chronic. Springsteen definitely noticed the negative reception to the song, and hasn’t played it at a live show since the year it came out.

“Ur So Gay” – Katy Perry (2008)

It’s surprising to find this song is still available to stream, given how poorly it’s dated. From the cruel suicide reference in the first verse to the obvious positioning of “gay” as a negative quality, “Ur So Gay” is a blight on Perry’s mostly stellar pop canon, along with the fetishising “I Kissed a Girl”, which appears on the same album.

“Driftin Too Far From Shore” – Bob Dylan (1986)

The title of Dylan’s 24th record should give away what kind of state he was in when he recorded this haphazard number. “I had no connection to any kind of inspiration,” Dylan wrote about this uninspired period, in his 2004 memoir Chronicles. “My own songs had become strangers to me. It wasn't my moment of history anymore. Try as I might, the engines wouldn't start.”

“Blow” – Chris Stapleton (with Ed Sheeran and Bruno Mars) (2019)

I can’t imagine what possessed Chris Stapleton, one of the greatest living country music artists, to join in with this teeth-grinding, face-melting display of faux rock’n’roll machismo, from Ed Sheeran’s No 6 Collaborations Project. It’s a bizarre approximation of something Aerosmith might have churned out on a bad day, complete with pat lyrics about a nameless “woman” who’s a “supernatural freak”. It’s also a resurfacing of every sexist cliché rock music was supposed to have left behind by now: “You red leather rocket, you little foxy queen,” Mars howls. Then there’s the chorus, which turns the gun into an obvious metaphor for, well, you know. “Locked, loaded, shoot my shot tonight,” they sing. “I'm comin', baby/ I'm gunnin' for you/ Pull my trigger, let me blow your mind.” Excuse me while I throw up.

“Yummy” – Justin Bieber (2020)

This song is what happens when you write a song for all the wrong reasons. Released just as artists were learning of TikTok’s potential to boost a song’s popularity, “Yummy” is an insipid and absurdly childish declaration of affection. “Yeah, you got that yummy-yum/ That yummy-yum, that yummy-yummy/ Yeah, you got that yummy-yum/ That yummy-yum, that yummy-yummy,” Bieber sings. Suddenly I’ve lost my appetite.

“Whatzupwitu” – Michael Jackson ft Eddie Murphy (1993)

This oddly soulless tune was accompanied by a comically bad video that showed Murphy and Jackson frolicking around a CGI sky, while cartoon peace signs float past and a choir of schoolboys dance around them. The lyrics themselves are painfully dated; Jackson’s delivery of the refrain “Whatzupwitu” is peak, “How do you do, fellow kids?”

“Mood Ring” – Lorde (2021)

David Bowie once called Lorde the “future of music”, thanks to the impact she made when she released her single “Royals”, aged 16. Two excellent albums followed: her debut, Pure Heroine, in 2013, and Melodrama, in 2017. Imagine the disappointment, then, when she returned with Solar Power last year. Inspired in part by the Nineties music Lorde grew up on, it’s astonishingly dispassionate and in places completely devoid of inspiration. This is perhaps best encapsulated on “Mood Ring”, on which she literally sings: “I can't feel a thing/ I keep looking at my mood ring/ Tell me how I'm feeling.” It doesn’t help that Lorde is delivers the track in breathy vocals that come off as twee when accompanied by summery guitar strumming that, ironically, leaves the listener cold.

“Filthy” – Justin Timberlake (2018)

The “SexyBack” singer was widely mocked when he returned in 2018 with his fifth studio album, Man of the Woods. The title promised some kind of stripped-down, reflective sound, amid scrutiny of the pop star’s appropriation of R&B over the years. Instead, he offered cheap approximations of past hits, with electronic beats and, in the case of opener “Filthy”, the kind of remarks that get you kicked out of the club and onto the sidewalk.

“Cars Are Cars” – Paul Simon (1983)

What was Paul Simon thinking? Under pressure to record the follow-up to 1970’s Bridge Over Troubled Water, Simon came up with this tragically naff track. It was supposed to make a point about how, deep down, humans are different all over the world, unlike cars. Yikes.

“Lolita” – Lana Del Rey (2012)

The US artist frequently explores themes of sexuality and the taboo side of relationships, but this on-the-nose track from her debut album, Born to Die, was far too literal. It was also oddly rushed, with Del Rey singing over a chaotic, industrial-style beat.

“My Ding-a-Ling” – Chuck Berry (1972)

Chuck Berry is one of the most influential rock artists of all time, but even he came up with a dud in the form of “My Ding-a-Ling”, a lewd but oddly childish number about his penis. It’s bizarre to think it almost topped the charts in the UK (devastatingly, Berry’s biggest hit across the pond), beaten only by Little Jimmy Osmond.

“Do What U Want” – Lady Gaga ft R Kelly (2013)

This song wasn’t so bad in terms of the music itself, but more for the combination of the lyrics (“Do what you want with my body”) and Gaga’s chosen collaborator, who has since been convicted of multiple sex crimes. “As a victim of sexual assault myself, I made both the song and video at a dark time in my life… my intention was to create something extremely defiant and provocative because I was angry and still hadn't processed the trauma that had occurred in my own life,” Gaga said in an apology issued in 2019, following the release of the documentary Surviving R Kelly. “I think it's clear how explicitly twisted my thinking was at the time.” She has since reissued the song, now as a duet with Christina Aguilera.