Janelle Monae kissing diddyRick Ross has been making interesting changes to his Maybach Music Group label lately, signing Wale in March 2011 and officially signing Midwestern emcee Stalley. Listeners of their music may be surprised that they landed deals with Rick Ross, whose music is known for its  lavish imagery. Still, rap history has had many other free agent signings that were just as odd to see. Read below for more.

Janelle Monae to Bad Boy Records

After getting her buzz up by appearances on Outkast’s Idlewild and gaining fans with her eccentric style, energetic live performances and conceptual Metropolis: Suite I (The Chase), it seemed common assumption that Janelle Monae would sign with Big Boi’s Purple Ribbon imprint. Instead, the songstress signed to Bad Boy Records under Sean “Diddy” Combs—a mogul who has had former signees launch fan campaigns to free them from the label (The LOX), write books about shady business practices (Mark Curry’s “Dancing with the Devil”), sever ties while in prison (Shyne), and a laundry list of other dubious deals.

Result:

Janelle Monae isn’t a household name just yet, but her first two Bad Boy releases—the re-released Metropolis: The Chase Suite (Special Edition) and The ArchAndroid—have kept her artistic integrity intact, surprising many die-hard fans that expected Diddy to water her down. She has also garnered a Grammy nomination, festival appearances, tours with the likes of No Doubt, and placement on the 2009 season finale of American Idol. The rest of her career is yet to be seen, but she’s already trumped Diddy’s “Making the Band” outcasts.

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Snoop Dogg to No Limit Records

Calvin Broaddus earned his rep in rap as a West Coast rider. With albums produced by Dr. Dre, guest appearances alongside 2Pac, Death Row Records as his label home, and music videos of him stomping through New York City, Snoop defined what many hip-hop heads will always recognize as the California sound and image. So things were a bit weird when he got out of his Death Row deal and signed to No Limit, Master P’s fledgling label based in New Orleans, La.

Result:

Snoop’s albums with No Limit continued to gross high record sales with their star power and Master P’s genius branding, but the critical reception was mixed. Da Game Is To Be Sold, Not To Be Told is widely acknowledged as one of his worst albums, but No Limit Top Dogg and Tha Last Meal did a better job of sticking to his West Coast roots with guest appearances and production by Dre, Soopafly, Kokane, Battlecat and more. It’s also arguable that Snoop’s transcendence as a pop culture icon began around his time with No Limit as well.

Teena Marie to Cash Money Records

Before she passed away in December, Teena Marie was a legendary R&B/soul singer who was signed to Motown Records in the late 70s/early 80s, and Epic/CBS Records until 1990. Known for her collaborations with Rick James and her soulful voice, Marie was dubbed as the “Ivory Queen of Soul.” Such an established artist of her tenure wouldn’t ever fit in on the “Classics” sub-label Lil Wayne and Baby “Birdman” Williams’ Cash Money Records, then, right?

Result:

While many were perplexed by the move, her results weren’t as bad as someone may have expected. La Dona earned a gold certification with its sales and became the highest-charting album of her career, peaking at no. 6 on the Billboard 200. She was also nominated for a 2005 Grammy Award for the single “Still In Love.” Not bad for her first album with Cash Money, and her first official album since 1994’s Passion Play. Her last album with the label, Sapphire, didn’t perform as well, but still got some positive reviews.

Nas to Def Jam

Nas and Jay-Z had one of the most memorable beefs in hip-hop history. Nas accused Hov of biting styles, disrespecting his own fallen comrade and “selling (his) soul for riches,” while Jay dissed Nas’ rap catalog and called out his baby’s mother for being promiscuous. So it surprised many that Nas would sign to Def Jam Records in 2006, two years after when Jay-Z was named president of the label.

Result:

Nas’ album Hip-Hop Is Dead definitely showcased its Def Jam production budget, supplementing longtime collaborators L.E.S. and Salaam Remi with the likes of Scott Storch, will.i.am and Kanye West. The album also got generally positive reviews and a Grammy nomination, but to some, felt too much like Nas was trying too hard to make a “Def Jam album.” Untitled and Distant Relatives garnered the most attention, though. The former used a controversial original title of ”N****r” to bring ears to its detailed dissertation of black history, and the latter was a joint album with Damien Marley that fused hip-hop with reggae and covered African ancestry, poverty and the diamond trade.

Pusha T to G.O.O.D. Music

Despite GLC (Gangsta L Crisis) being one of G.O.O.D. Music’s founding artists, most media and fan praise for Kanye West and his label was rooted in it being an antithesis to street rap. Up until last year, previous signees had included “conscious” emcee Common, R&B vocalist John Legend, emo rapster Kid Cudi and fly kid Big Sean. So despite having an assorted clientele of emcees he lent beats to, many were surprised to see Kanye sign Pusha T, who had earned a rep for drug-pushing raps as half of Clipse.

Result:

Pusha T made his official GOOD Music debut on Kanye’s “Runaway,” and it was obvious from there that their musical marriage would be beneficial to both of them. Aside from Ye’s superior soundbeds matching the Virginia emcee’s mic presence, Pusha’s cold-hearted rhymes perfectly coincide with the cocky demeanor that his new label head often assumes. The chemistry was further solidified by Pusha’s enjoyable Fear of God mixtape.

Honorable Mention:

Peedi Crakk to The Roots

In retrospect, Peedi Crakk joining The Roots makes sense with them both hailing from Philly and with Jay-Z having a working relationship with the band. Still, it was surprising to see a Roc-A-Fella emcee whose name implied selling drugs join forces with a Grammy-nominated act known for their conscious, introspective lyrics and envelope-pushing content. While this isn’t a label signing like the other five it stands out as one of the oddest pairings we’ve ever seen.

Result:

Ever since he made his Roots debut on Game Theory, Peedi has shown an incredible chemistry with the group. His energetic, high-pitched voice deftly contrasts Black Thought’s tough-as-nails vocals, and his melodic delivery meshes with the group’s live musicality. Two of the three Roots albums he’s been a member for—Game Theory and How I Got Over—were nominated for Grammy awards, and all three of them (including Rising Down) have been critically acclaimed as worthy additions to their already respectable catalog.

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