The freestyle is one of hip-hop’s oldest and purest challenges, vital for an MC to earn their stripes in the game. The ability to effortlessly deliver rhymes straight off the top is a skill equated with one’s talent, largely implying a degree of merit when someone can really drop that heat on the spot. On the flipside, when a rapper falls short upon delivery, it's grounds for an unapologetic roast session (a la Eminem in the beginning of 8 Mile).

Actors, by nature, are also thrown into a world very similar to freestyling, with the ability to improvise on stage or on camera integral to their success. Sometimes these worlds collide, with actors being called on to offer their best attempt at rapping. The results are often mixed, but every now and then, as Lupita Nyong’o proved earlier this week, actors can hold their own in a freestyle and shouldn’t be written off as a one-trick pony.

When a comedian, such as Amy Schumer or Craig Robinson, tries his or her hand at a freestyle, it often makes for some of their best material because it's so damn funny. Even a bad freestyle can add some lighthearted humor into the mix and be appreciated by all. But the likes of Will Smith, who spent his career earning respect while moving between the worlds of hip-hop and Hollywood, and The Night Of star Riz Ahmed, who also wears a hat as rapper Riz MC, do their best to make sure their talents on the mic are nothing less than stellar.

While actors freestyling can be hit or miss, you have to give it up to them for trying. From Seth Rogen to Leonardo DiCaprio and more, watch these 11 actors spit a freestyle.

  • 1

    Shia LaBeouf

    Shia LaBeouf has some bars in this clip, but what’s more impressive is that he keeps going throughout it all, giving some real deal rappers serious competition with the amount of time he goes for. He even name-drops the film Transformers, one of his biggest claims to fame as an actor.

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    The actor then redeems himself during a visit to Sway in the Morning, where he takes part in the Five Fingers of Death freestyle challenge. LaBeouf, who's got tattoos of Tupac, Biggie and Missy Elliott, bodies this freestyle, proving he can give some of these rappers out here serious competition.

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  • 2

    Tyler James Wiliams

    Tyler James Williams was inspired by Drake’s “6 God,” leading Sway, on his Sway in the Morning show, to share quite the reaction when the actor asks if they could drop the instrumental. The radio host is then pleasantly surprised when Williams drops his freestyle, proving he could have quite the career as a rapper ahead of him if he so chooses.

  • 3

    Seth Rogan, Anthony Mackie and Joseph Gordon-Levitt

    These gentlemen sharing the mic is a must-see. The three actors were challenged to somewhat of a freestyle battle during Sway in the Morning, equally dropping bars and laughter along the way. Seth Rogan brings Sway to tears with his "smelly" lines while Joseph Gordon-Levitt sort of sings his way through it and Anthony Mackie tops them all.

  • 4

    Lin-Manuel Miranda

    Jimmy Fallon put Hamilton creator Lil-Manual Miranda to the test, playing a game where he challenged the writer to freestyle while including the words “rainbow,” “pancake” and “slam dunk.” Lin-Manual rose to the challenge, even managing to weave Drake and Michael Jordan into his freestyle.

  • 5

    Craig Robinson

    Craig Robinson drops a freestyle while radio host DJ Whoo Kid uses his beatboxing skills in the middle of this interview. Peep the 10:30-mark to hear Craig’s wavy freestyle, in which he includes some of his accolades as a comedian and an actor.

  • 6

    Joseph Sikora

    Joseph Sikora, better known as Tommy on Power, dropped by Shade 45 and ended up rising to the challenge of dropping an insane freestyle around the 17:30-mark.

  • 7

    Patrick Duffy

    Patrick Duffy was given a lesson in freestyling on Sway in the Morning. The crew even gave him the rap name MC Fanny Pack Boy before challenging him to drop his first ever freestyle. Check in around the 8:45-mark to see how things go down.

  • 8

    Amy Schumer

    Amy Schumer hilariously failed while trying to impress Method Man during the filming of her romantic comedy Trainwreck. She has a couple of opportunities to shine but doesn’t quite rise to the occasion. Fortunately for her, Meth isn't too harsh.

  • 9

    Amy Poehler

    Amy Poehler is no stranger to the freestyle rap battle, often interrupting her rap flow with her signature laugh. Her content is as hilarious in freestyle form as it is during her stand-up comedy and writing. She definitely has a way with words.