Flirting With 50 Cent: A Selfie Guide To Fif's 15 Favorite Ladies

Fif has posed with a number of big-name dames, from Oprah to Rachael Ray.

By Phillip Mlynar

During his rise to mega-stardom, 50 Cent has clocked up many milestones: He's been the universe's one-time most dangerous rapper, blazed trails by shifting a now legendary 872,000 first week copies of his debut album, Get Rich Or Die Tryin', made a gazillion bucks from a savvy Vitamin Water endorsement deal and, now, he's successfully transitioned over into the world of film.

Fif's biggest achievement though is surely the collection of selfies he's amassed alongside famous femmes. Glancing through Fif's impressive Instagram account is like rummaging through a complete collection of Pokemon cards -- when it comes to posing with daytime talk show staples and legendary ladies of the silver screen, 50's scored them all.

In tribute to the rap king of the celebrity selfie, here's a round-up of 50's 15 favorite ladies. (You can draw your own conclusions as to whether any romantic trysts ensued.)

1. Meryl Streep

A classic power-move from the top of this year, 50 Cent spotted legendary Oscar collector Meryl Streep at a Knicks versus Lakers game. With the smooth and steely moves of a predatory panther, Fif moseyed on up to Meryl and pulled out his hand-holding flirt tactic courtside. Then he took things backstage where, as he put it, "Things got a little gangsta. Lol TURN UP, Turn Down for what!"

2. Rachael Ray

There's a kittenish first-date vibe to the series of snaps that emerged of 50 and modern family kitchen maestro Rachael Ray cozied up together after an appearance on her TV outlet.

"[Rachael] Ray is the best I had a ball on her show," gushed a grinning Fif', although it's unclear if Curtis now spends his Sunday afternoons rockin' out on bass with Rae Ray's rock musician husband, John Cusimano, in the family garage.

3. Sheryl Crow

When titans of the rap and pop/country worlds meet up, they always like to don their most formal of wares. Which is exactly what Fif did when he cavorted around with Sheryl Crow.

Beyond the smart surface sheen though, all might not be well in the Curtis and Sheryl relationship, as he captioned his pic with the back-handed compliment, "This woman Sheryl Crow is beautiful in person." Possible cat sound?

4. Renee Graziano

50 Cent might move in high-profile Hollywood circles these days, but he's always willing to prove that his street ties are still fully operational -- as when he selfied it up with "Mob Wives" player and La Cosa Nostra connect Renee Graziano. Having hashtagged the pic #MobCandy, what price Ms. Graziano appearing as a video vixen in 50's next music flick?

5. Bette Midler

Part of the charm of 50 Cent's Instagramming talent comes from the way he seamlessly segues between disparate worlds. So after posing with the Mob Wives madame Renee Graziano, he proved he's equally at home showing his stately and suited-up credentials with the respectable all-around entertainment vehicle Bette Midler. And if you were wondering, Bette is one of 50's most favorite people in the whole wide world.

6. Oprah Winfrey

With his chipmunk grin and cocksure swagger, 50 Cent is far from humble. He aired out his stuntin' side when he received a chance to sidle up to pop-culture deity Oprah Winfrey -- a declaration of status that he couldn't resist bragging about: "Ok I think I blew up and nobody told me anything. Now I'm mad, I'm hot don't talk to me.Lol." Rolling on the floor laughing, Fif, literally rolling.

7. Melissa McCarthy

Wild pitch: 50 Cent is a fanatic of the movie "Bridesmaids." So much so that when he ended up on set with actress Melissa McCarthy while filming the movie "Spy" together, he just couldn't resist engaging in one of his Hollywood fantasies and putting the moves on her.

In Fif's own words, he kept it classy as he wooed her with nothing less than modern romantic poetry: "I said Melissa I'm attracted to you, so I'm gonna need your room #. She gave me this look like you not ready. Oh I'm ready lol." We suspect another type of rolling on the floor ensued.

8. Chaka Khan

Few things phase 50, but when he was offered the opportunity to add a pic with legendary R&B diva Chaka Khan to his selfie collection he definitely seemed to retreat into his shell a little. In fact, here 50 looks straight-up shook -- although that velvet suit might just have been a little on the scratchy side.

9. Kim Kardashian

Culled from 50's vintage selfie folder, here's a pic that he breezily calls "Me and Kim K kicking it." The idea that he posted it recently as a not-at-all veiled barb towards Kim and Kanye's upcoming nuptials is totally unsubstantiated.

10. Rose Byrne

Proving that he's a global selfie connoisseur, Fif mugged it up with Australian actress Rose Byrne, of "X-Men: First Class" fame. Trivia tidbit: Rose was born in Balmain, although the city is not twinned with Kanye's favorite fop, Pierre Balmain.

11. Terri Hatcher

A lesson in the art of the intriguing selfie, here 50's coyly-raised eyebrow juxtaposes with Terri's frog-wide grin. It's a bewitching combination that leaves you wondering at what point 50 offered to don his Gatman costume and play nicely with a Lois Lane-outfitted Terri?

12. Joan Rivers


"The Amazing Joan Rivers lady's and gentlemen," is how 50 introduced this uproarious selfie with the ambitious comedienne and actress. Reports that 50 based his early career image on advice given in

Rivers' books "Diary of a Mad Diva" and "Jewelry by Joan Rivers" have never been outright denied.

13. Lucy Walters

Another selfie sourced from the folder that 50 cryptically calls "Girls on Film," here the Queens rap icon has paired a bold checkered blazer with a hometown baseball cap in a bid to woo the actress who came to repute after a silent starring role in Steve McQueen's Shame. "Lucy Walters is amazing," 50 was moved to remark as he held a studious thespian pose to the camera.

14. Naturi Naughton

Is there a deep meaning behind 50 taking off his signature baseball cap to pose with the actress (and former member of R&B troupe 3LW) Naturi Naughton? Also note the wandering right hand, which is less clasped around Ms. Naughton's waist as ready to roam. This selfie is worthy of prompting some fine Fif fan-fiction.

15. Gayle King

Over the years, 50 Cent has played a high-stakes game of flirting by switching his attention between Gayle King and her BFF of all BFFs, Oprah Winfrey. After posing with Gayle, Fif was moved to take to his Twitter account and offer this compliment: “She’s perfect. Her thighs define sexy, her hips are just right, her eyes talk to me. Oh and her ass."

Is there a long-term romantic future on the cards between Fif and Gayle? Who knows, but if there's one shotgun celebrity wedding that would upstage Kanye West and Kim Kardashian's impending shindig...