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No rapper is perfect, not even any of the greats. Eminem, one of the most critically acclaimed, commercially successful rappers of all time, has released his fair share of truly terrible songs over the years, yet his overall legacy hasn’t suffered for it. Still, there’s no point in pretending those dud tracks were any good. They most certainly were not.

Eminem has been making music for more than a quarter of a century. He’s released 12 studio albums, a couple of compilations, and, weirdly, only a single EP—1997’s Slim Shady EP being the only one. That’s to say nothing of his collaborations, be it as part of D12, Bad Meets Evil, or any other partnerships he’s embarked upon over the years. The point, in any case, is that he’s released a lot of music, so it’s only natural that, amid all the glittering jewels of songs, there have been some failures, too.

Eminem doesn’t shy away from his own music that he feels falls short of the mark. Referencing his song ‘We Made You’ on the later track ‘Guts Over Fear,’ Em raps, “There’s no more emotion for me to pull from / Just a bunch of playful songs that I make for fun / So, to the break of dawn, here I go recycling the same old song / But I’d rather make ‘Not Afraid 2’ than make another muthafuckin’ ‘We Made You.’”

To be fair, it’s all a matter of taste. ‘We Made You’ is a fun song, if not the height of sophistication, and lots of people are into it, even if its creator is not. It’s not an exact science to select an artist’s best and worst moments, but, at the same time, there are outliers that tend to stick out in people’s minds. In Em’s case, there are quite a few stinkers that are difficult to ignore. Here are five of the worst culprits.

The five worst Eminem songs:

5. ‘Those Kinda Nights’ featuring Ed Sheeran 

Here is a track that just doesn’t sit right. It’s true that Ed Sheeran has become about as big a global superstar as it’s possible to be, but still, it’s difficult to view him as anything other than a nice English boy who got quite good at the guitar. To hear him on a track with Eminem—a man who became famous for making songs about killing his wife and for wielding a chainsaw on stage—is fairly odd anyway, but for that particular song to be focused on a night out in a strip club is just, frankly, uncomfortable. It doesn’t suit Ed.

Sheeran and Eminem had, by this time, already worked together on Em’s song ‘River’ and on Sheeran’s track ‘Remember the Name,’ which, indeed, sees Sheeran going full-on braggadocious and showing off about how big an artist he has become. He demands respect, and, to underpin the point, he wheels out Eminem and 50 Cent, thus illustrating his industry—and even hip-hop—credentials. Fine. But it still feels odd.

4. ‘Puke’

This will not be the only track from Eminem’s 2004 album Encore to be included on this list, and there could easily have been several others, too. Even Eminem himself has admitted that his fifth album was one of his weakest efforts, and, while it does have some great songs on there, it boasts a healthy number of absolutely awful ones, too. ‘Puke’ is certainly among the most egregious, with Em seemingly determined to actively upset his listeners by including the vivid sound of someone throwing up into a toilet. It’s horrible.

But it’s not only the puking sounds that make the track so bleak to listen to. It’s just bad, be it musically or lyrically. It’s yet another vicious song aimed at his on-off wife Kim, but it falls far short of predecessors like ‘’97 Bonnie & Clyde’ and ‘Kim,’ which, while cruel and twisted, are certainly works of art. ‘Puke’ instead features lines like, “I knew I shouldn’t go and get another tattoo of you / On my arm, but what do I go and do / I go and get another one, now I got two / Ooh ooh ooh ooh ooh ooh ooh.” It’s almost like Em forgets that people are going to listen to this thing some day.

3. ‘Heat’

Perhaps the only other album to give Encore a run for its money in the battle to be crowned Eminem’s worst is 2017’s Revival. While it’s not as aggressively offensive to listen to as parts of Encore are, it’s just generally quite weak throughout.

It features a lot of pop stars, and musically, it has some of the thinnest production of any Eminem project ever. There are quite a few songs on there that are lacking in oomph, but ‘Heat’ is arguably the worst offender.

Built upon a cheesy rock-driven beat, it’s difficult to tell if the song is meant to play as a novelty track or not. It’s bad enough to be one, but it’s not even funny. Eminem has gotten away with some outrageous songs over the years, and the reason is that, at his best, he’s an extremely funny songwriter. But this track isn’t even funny, in addition to sounding kitsch and being lyrically banal.

2. ‘Ass Like That’

Another one from Encore, ‘Ass Like That’ is another deliberately offensive effort that can’t hide behind the fact that it’s funny, because it just isn’t. To be fair to him, Eminem has explained why this song, and others from Encore, were as bad as they were, telling Rolling Stone in 2011, “Around the tail end of Encore, the songs started getting really goofy. ‘Rain Man,’ ‘Big Weenie,’ ‘Ass Like That’, that’s when the wheels were coming off. Every day I had a pocketful of pills, and I would just go into the studio and goof off.”

This period was at the height of Eminem’s drug addiction, and those bleak circumstances fed into Encore’s chaotic, often surreal tone. While that’s a sad fact of what was going on in Em’s life at the time, the album nonetheless must be judged on its own merit, and there are many moments where it doesn’t stand up to scrutiny. ‘Ass Like That’ is one such moment, a diss track aimed at a puppet, Triumph the Insult Comic Dog, that features Eminem adopting vague foreign accents. Its great crime is less that it’s insulting to anyone in particular, and more, simply, that it’s rubbish.

1. ‘Fack’

It had to be this one. Even Eminem recognises how bad ‘Fack’ is, as he made clear while promoting his last album The Death of Slim Shady (Coup de Grâce). In collaboration with Complex magazine, Em put together a skit in which he and his younger alter ego, Slim Shady, sit down to face off against each other, during which time they blame each other for the regrettable creation of ‘Fack.’ No wonder. It’s a terrible, terrible song. Not only is it digusting, listening to Eminem, or Slim Shady, or whichever version of himself is in charge here, fighting off an orgasm is quite an unpleasant experience, but it’s also profoundly irritating. 

All that can be said for ‘Fack’ is that it’s bold. This was one of only three new tracks to be included on Eminem’s greatest hits album Curtain Call, which, by its very nature as a greatest hits record, was aimed at mainstream audiences. Not only that, but it was the very first track. That means that people who just wanted to hear ‘Lose Yourself’ would have been subjected to this filth. As Slim says in that Complex video, “Not only do we make one of the worst songs ever, but we put it on the greatest hits album. Not only did we put it on the greatest hits album, but we made it the first song on the greatest hits album. If that doesn’t take balls, what the fuck does?”