50 Cent: In a moment of money-grabbing madness 50 Cent appeared on TV shopping channel QVC in 2012 to help sell his brand of 'SMS' headphones. Afterwards he bragged about making nearly $200,000 from the plug - but he'll never be able to buy back what little dignity he had left.
Snoop Dogg: He's famous for featuring on the tracks of countless pop artists. But perhaps the most ill-advised was when Snoop appeared in the video for 'Boyfriend', a track by teenage boyband Big Time Rush. Snoop can normally pull most things off but this time he took it too far.
Ice Cube: In the late 1980s Ice Cube was the one of the coolest men in hip-hop when he was one quarter of ganster rap trailblazers, NWA. But a few year's later his cool rating dropped considerably when he took up an an acting career starring in a series of inexcusably bad US sitcoms. Here he is on the cover 'Are We Done Yet?' No we don't remember it either.
Lil Wayne: When he featured in the video for Drake single 'The Motto', Lil Wayne looked more like a pampered Ox-Bridge student than a prophet of the ghetto as he was seen sporting a pair of bright green Ugg boots.
Dr Dre: The super-producer is widely recognised as one of the coolest men in music. But that wasn't always the case. In the early 80s before he formed NWA Dre was more into mascara and silk two-piece suits as a member of old skool electro group, World Class Wreckin' Cru.
Ol' Dirty Bastard: In 1998 eccentric/mentally unstable rapper and Wu-Tang member Ol' Dirty Bastard was arrested for shoplifting a $50 pair of trainers in Virginia. The bizarre thing about the robbery was that the rapper had more than $500 on him at the time.
Flavor Flav: A multi-instrumentalist from an early age, Flavor Flav came to prominence as the hype man for Public Enemy. Since then Flavor has gone on to star in a number of MTV reality shows, including Flavor Of Love, which involved Flav searching for his other half. In one episode one of the girls poos on the floor, for some reason, prompting this reaction from Flav.
Lil Jon: Every discerning rapper needs to take time out to make some easy money on the side. In Lil' Jon's case that involved shouting 'YEAH' in between mouthfuls of sandwich to agree with other diner's praise for Subway.
Jay-Z: In the early 2000s rappers Jay-Z and Nas were locked in one of the most closely followed feuds of the genre's history. Jay-Z eventually appeared to come out on top, explicitly detailing his affair with Nas' girlfriend of the time on 'Super Ugly'. That was until his mum heard the lyrics and demanded that Jay-Z apologise to Nas.
RUN-DMC: They are one of the bands credited for pretty much inventing hip-hop. Famed form their lether jackets and ghetto image they would be near the top of many people's cool lists. But in 1999 they altered the lyrics to their hit 'Peter Piper' to perform on a TV advert for high street clothing retailer, Gap. Needless to say it did more for Gap's sales than RUN-DMC's coolness.
T-Pain & Taylor Swift: Even for an auto-tune addicted rapper like T-Pain, a collaboration with country starlet Taylor Swift seems strange. In what can only be a joke, Taylor raps "I'm like 8 foot 4, blond hair to the floor/you shorties never thought I dreamed about rapping hardcore/no I ain't got a gun/no I never really been in a club/still live with my parents/but I'm still a thug." Either way, it can't have done much for either artist's careers.
Ludacris: In 2010 Ludacris was really struggling for ideas when rather than call up one of his friends from the hip-hop world, he instead headed down to the bowling alley with a load of teenagers to collaborate with the king of uncool, Justin Bieber... Ludacris indeed!
Dr Dre's Beats company is set to launch a new music streaming service to rival the likes of Spotify and Deezer. Not very embarrassing in itself, but the name? Dre and collaboratro Trent Reznor of Nine Inch Nails have decided to call the new service 'Daisy' - which is not very hip hop in the slightest...