The Ten Freestyle Rap Commandments


New York’s hip-hop scene had plenty of surprises in 2014, the most unexpected of which was probably the return of freestyling. What was once considered a niche pastime or endangered art form has found new life through fans rediscovering the joys of both extemporaneous wordsmiths creating new works in front of their eyes, as well as established MCs rekindling their love of freestyling itself.

Manhattan’s home to two weekly free freestyle events, the Lesson’s open-jam show Thursdays at Arlene’s Grocery (95 Stanton Street), and Union Square’s Legendary Cyphers, an outdoor open-door policy cypher that has its season finale this Friday. There’s also been the return of the monthly Spike Hill (184-6 Bedford Avenue) battle/open-mic Freestyle Mondays on the first Monday of every month, which has kept freestyling alive for 13 years.

See also: Legendary Cyphers Bring Hip-Hop Back to Union Square Park

Freestyling’s also become hot in the comedy world. The Pivot network gave a weekly half-hour Friday-night show to rhyme improv experts Freestyle Love Supreme. North Coast has had a repeatedly extended weekly freestyle show at the Peoples Improv Theater (123 E 24th Street). UCB East boasts Battlicious, the monthly freestyle comedy rap battle.

Even the bigger names in indie rap, like New York’s Homeboy Sandman, Minneapolis’s Atmosphere, and Los Angeles’ Open Mike Eagle, have made freestyling a regular part of their live shows (with all three enjoying a thunderous reception at their most recent New York concerts).

See also: Homeboy Sandman’s Rise Took a Lot of Work

If you’ve caught any of the freestyle action in person, there’s a chance you’ve been curious to try it out. Given how much fun we think freestyling is, we’ve put together this list of 10 things every freestyle rapper should know.

Here are our 10 freestyle commandments:

1. Start Rapping At some point, even the world’s most gifted freestylers were hesitant to rap in front of people. The first step to becoming a quality freestyler is…attempting a freestyle for the first time. Before you get into consummate conceptual wizardry, you need to become comfortable rapping on the spot. Freestyle Mondays host iLLspokiNN advises, “Rule number one is to be free. Let go of the driver’s wheel and don’t try to control the thought patterns until you get to a point where you can.”

2. Know When to Stop Rapping and When to Start Again Say you’re with a group of friends or total strangers, rapping. The beat’s boomin’, people are groovin’ — and you’re not sure when to come in. This is where what’s known as “cypher etiquette” comes into play. While there are no defined rules (it is a freestyle, after all), you’re most likely to have a natural entrance coming in after someone’s rhymes hit some multiple of four (jumping in after the fourth, eighth, or 16th line is most common). If someone starts rapping in the middle of your verse, don’t take it personally. They didn’t “cut you off.” That’s just how cyphers work. Don’t tell them to hold off, just roll with it.

3. Get Comfortable With Freestyling in the Moment Now that there are more opportunities than ever to freestyle, practicing will help you become in tune with the skill to let the words pour out. Here’s UTK of Freestyle Love Supreme: “The actual act of freestyling requires a complete openness to allowing whatever to happen in the moment occur without self-judgment…The minute you try and control it, you are cutting off the possibility of surprising the audience — and, most importantly, yourself.”

4. Always Be Thinking Ahead Does this seem like we’re contradicting the last suggestion? Well, not really. You can still plan ahead while you’re living in the moment to make sure your freestyle maintains consistency. As Battlicious host Victor Varnado (a/k/a “King Supernuts II”) suggests, “End on a punch that surprises the audience. Better to leave the best part for the end. [If] I want to diss Bill Cosby…I think of something that rhymes with his Cosby character and then I use that to lead up: ‘I’m Al Capone in here and you think you’re untouchable/But you’re gonna fall from grace just like Cliff Huxtable.’ ”

5. Keep Rapping Freestyling can be tough. Heck, anything can be tough, discouraging, and make you want to give up. Given the understandably spontaneous nature of freestyling, this instability also affords you plenty of opportunities for recovery. Freestyle Mondays’ only 18-time champion, Rabbi Darkside, assures us, “If you get stuck or stopped, find the groove again and keep going. You can generally rap your way out of stalls, especially when first starting.”

6. Control the Moment; Don’t Let the Moment Control You It can be overwhelming when you’re freestyling and everything falls into place, so maintaining order is important. As The Lesson host Phase One tells us, “This goes for when you are doing good in a rhyme and reach a peak and get the ovation but it’s hard to keep that consistency. You’re hyped off the hype, or vice versa when the vibe is wack — it can affect the freestyler as well.”

7. Don’t Panic Let’s say you’ve started rapping, but suddenly your mind goes blank, your hands shake, and the only sound you can emit is an “uhhhh.” Or worse, you don’t feel like your rhymes are going anywhere and you’re losing your timing. Or perhaps you just passed the mic to crickets and you don’t think you can ever rap again. Relax, homie, it happens. Here’s Homeboy Sandman on the matter: “Don’t let imperfection frazzle you. Your next great line, and all of the ‘ooh’s and ‘ahh’s it will induce, are right around the corner.”

8. Don’t Be the White Guy Rapping About Being a White Guy You’re a white MC; regardless of how impressive this might be to you, don’t be obsessed with your own whiteness. That’s not to say caucazoids drawing from their particular cultural heritage is frowned upon — quite the opposite, really. Proud that you’re Irish? Russian? Swiss? Knock yourself out. Specifically, the problem is when white freestylers feel compelled to keep everyone aware that “I’m just a white boy in the cypher” or to refer to the other white MCs who might be in the cypher as “the other white boys here.” It’s uncomfortable because it’s painfully uninteresting. This is the least important commandment on this list, but the less this happens, the better time everybody’s going to have.

9. Trust That It’s All Going to Work Out If you haven’t freestyled much, the idea of creating rhymes on the spur of the moment can seem daunting, or downright scary. That’s why it’s important to just dispose of your misgivings and put your faith in the rhymes flowing through you. Legendary Cyphers’ resident MC, Elijah Black, described it to us as “The less you think, the better the freestyle will be. Let it flow naturally.”

10. It’s Really, Really Fun The appeal of rapping itself means different things for different people. For some it’s skills, for some it’s storytelling, sharing an experience, spreading a message, etc. Ultimately, what draws us all to hearing rapping or participating in it is no different from how it was in the ’70s when hip-hop began. It’s about that good-time party feeling — even when the topics get serious, that shared experience of enjoying rap unites those of us fortunate enough to find it appealing. If you’re freestyling and a battle breaks out, you can respond and continue on, but don’t take it personal. If someone cuts you off before the line you wanted to say or you don’t get to jump in on the beat you wanted, the stars will align again. Every time you freestyle, the moment is what you make it, so make that moment whatever you want it to be. Life itself is a freestyle, but at least rhyming adds a certain comfortable foundation to the journey.