When the Doggfather popped up in season 4 of Entourage, the writers gave him this incredible line to describe the latest film starring Vincent Chase (Adrian Grenier): "I saw the trailer. Y'all make Blow look like [the children's show] Romper Room."
While Vince is playing Aquaman in season 2, the serial ladies man got sensitive off-camera with Aquagirl, who just happened to be his ex-girlfriend Mandy Moore. Years later, Ryan Adams aced out the fictional character for her hand in marriage.
After unsuccessfully hitting on Minka Kelly, Eminem's bouncer moved to toss Vince out of the party. The out-of-control actor lashed out at Mr. Mathers, asking him, "Are you too mainstream now to fight your own fights,
Marshall?" The answer: A swift punch to the jaw from the Detroit MC. You don't mess with Em.
50 Cent pulled up to Turtle's Ferrari at a stoplight to say hi (Turtle knows everyone) and make fun of him during season 6. I imagine this is how running into 50 Cent in real life might actually go down.
Just as Vince's agent Ari (Jeremy Piven) is about to treat his wife to a surprise party with musical guest Christina Aguilera, she calls him up and dumps him. Xtina's music becomes the soundtrack to his crumbling marriage in season 7. Bummer.
In this eighth and final season, Ari once again pays famous musicians to help him woo back his wife—only this time, it works. With the Italian operatic trio Il Volo on his side, Ari manages to repair his marriage in the series finale. Just try
to watch it and not get a bit teary.
Bow Wow (who played the up-and-coming comedian Charlie) had one of the all-time best guest spots during season 5. After getting a call from his agent, Charlie quit the Gap in bridge-burning style: "F-ck you crewneck wearing motherf-ckers! I just got my own
Kanye West swung by season 4 to fly Vince and his bros to Cannes on a private jet—replete with professional masseurs and a hotshot young airplane pilot named... Kanye West. "I took flying lessons a week ago and even though its
totally illegal, I'm going to fly us out of here," 'Ye told his terrified passengers.
Just before Ari got pranked by stripper cops, T.I. told him off for only offering him stereotypical rapper-actor roles: "Look at this sh-t, man. Gangster, drug dealer, rapper. I
might as well be playing myself," T.I. told Ari in season 5. "I want to do Black Sabbath. It's a story about
a young black supermarket checker who falls in love with an older Jewish woman. I'm thinking Meryl Streep. And it's set against the Crown Heights riots."
Sadly, this movie has yet to be made. Hopefully it will come to pass in the recently green-lit Entourage movie. You listening, Meryl? You know a love scene with T.I. is total Oscar bait.