Andy Samberg is how SNL maintains its contemporary edge, filling the role of a sort of rap-raised Jimmy Fallon/Adam Sandler. With his rap-parody group Lonely Island he makes digital shorts which at once parody and praise the genres Samberg is sincerely affectionate towards. And clearly everyone wants in on the joke, every host/musical guest from to Justin Timberlake to Arcade Fire to Lady Gaga joining in on the fun. Note all the guest appearances appearing on each of their two album releases.
It was the nineties, everybody was experimenting with it. No, not drugs: rap. And judging by the video (skateboarding dogs, backward hats, flannel, etc.) Tom Jones was just one more onboard the '90s paradigmatic express. Known for his Vegas showmanship and bra-tossing concert attendees, it seemed Jones was determined to stay in the panty-dropping business. Just take a listen at this song from 1993's The Lead and How to Swing It (and listen to that epic scream at the song's start) before Jones unleashes the dirtiest set of rhymes a '60s hitmaker ever has.
Donald Glover can do whatever he wants. He was part of wildly college-famous internet video troupe called Derrick Comedy, he attended NYU at the same time as he was writing for 30 Rock. He's succeeded at stand-up, and now--under the operative name Childish Gambino--he's a full-on rapper setting his comic wit to a beat. Which is to say he'll spit rhymes and jokes on two entirely separate tours.
R.E.M. are consistently good melody-craftsman. That's a given. And in the late eighties/nineties they had honed and distilled their craft to a point of regular radio-friendliness. And in doing so they merged genres traditional (e.g. folk, country, and psychedelic) and budding (i.e. rap) with skillful ease. "Radio Song" from 1991's Out of Time features rapper KRS-One (who Stipe was a fan of), and "The Outsiders" from 2004's oft-underappreciated Around the Sun features rapper Q-Tip in a similar marriage of African and European (folk) tradition. The results are surprising and amazing. "Michael Stipe and rap?" you question. Yes. Michael Stipe and rap. (Extra awesome: Michael Stipe actually performs the rap parts himself during live performances. See here starting at 2:55).
Pet Shop Boys specialize in synthesized dance music and biting social commentary. This seems fitting for a pair of posh Londoners who grew up in the suburbs. Unfitting is the unabashed rap influence, which Tennant grew up a fan of and channels pretty heavily in their earliest single "West End Girls" (1984). As city-weathered as the song's tone is--taking hints from Grandmaster Flash-- there's no avoiding the cultural vaccum that exists between the originators and casual adopters of the rap genre.
So apparently Phoenix never wanted to actually be a rapper, or a hobo for that matter, but was pursuing a life of oddball-dom for a phony documentary called I'm Still Here, for which real life became a sort of performance piece, as long as tabloids followed him around. Nevertheless, he did rap. And he sounds like a hypoglycemic Tupac.
U2 guitarist 'the Edge' is known for his use of delay. As in the delay that precedes an inevitable "Wait...what?" reaction upon hearing he actually rapped on a U2 track--i.e. "Numb" from 1993's Zooropa. While it may not stack up against Kanye or Jay-Z, the lyrics are delivered in a languid monotone, and it does kind of rhyme, which qualifies as being at least called rap. A band as set on radio-permeating, world-conquering success as U2, an absorption of concurrent trends is to be expected, even if sometimes painful indigestion ensues.
Bo Burnam was discovered the same way Justin Beiber was (even has the same hairstyle/skin complexion), he attended an all-boys' Catholic high school and pursued theater, and at 22, he is a multi-talented musical comedian, with a precocious wit and... dizzying rap skills. His word-smith skills are insane not just for someone of his age and background, but for someone who is primarily a comedian, his only record deals through Comedy Central. He's that good--toting an intellectualism that simply does not BELONG in rap--and it's all just for laughs. Make another song about genetalia Lil Wayne.
Nobody much expects a pirate-attired glam-post-punker to take equal parts inspiration from Elvis and the rap genre. Then again nobody much expected Adam Ant until his irresistability was proven, a chart-topper in the UK, and at once champion of past-and-present musical ideals. And while his signature drum sound with the Ants suggest tribal African influence, his lyrical technique suggests a more contemporary derivative of a traditional African stream of music. The man was a culture-sampler by every account (and a bit like Bowie, another audible influence, in that way). Take the song "Ant Rap" to hear his distinct take on the genre, and a little extra Renaissance'd up.
Blondie were very keen on genre experimentation--styles ranging from punk to ska to disco to new wave--so when Debbie Harry laid down some rhymes (albeit mostly simple words like 'car,' 'far,' and 'bar') for the song "Rapture" on 1980's Autoamerican, it wasn't a giant leap for the band. The track, as it turns out, was the first 'rap' song to top charts. (Then again, Debbie Harry could read a legal disclaimer and make it sound like heaven.)