The Top 5 Street Workout Money Moves

These exercises are for everybody who is ready for a unique physical challenge.

I was born in the summer of 1974 in deep Brooklyn, New York. I wasn’t athletic as a youth and did not play sports. My grade school was too broke to have teams, and the gym teacher was too abusive to support anyone’s ambitions anyway. This was 1980’s Brooklyn, which was a very different place than what comes to mind when you think of the hipster haven of today. The Brooklyn of my youth looked more like “Welcome Back, Kotter” than like season 4 of “Girls.”

The Determination to Get Strong

Like most young boys, I had lots of energy and a big desire to get strong in spite of my environment—or maybe because of it. Gyms were out, as we were too young and poor for them anyway, so I started out in fitness doing classic calisthenics exercises like push ups and sit ups on my own. I still consider these exercises to be two of the very best for people of all age groups and fitness levels.

Push ups lead to pull ups. Pull ups lead to dips. I inherited a dusty, old bench and some weights from an uncle. Soon bench press, curls, and military press were incorporated. Squats and deadlifts came later. I lifted weights for the next twenty years or so in conjunction with a steady, intense dose of calisthenics. The often-perpetuated notion that you must choose between external weight training or bodyweight training is one of the silliest concepts I’ve ever heard. The two are not mutually exclusive. They both make you strong, and work fantastically in conjunction with one another.

I was content with my hybrid training until the year 2006 when I saw something at a downtown park that blew my mind: a muscle up.

Game changer.

At this point, I switched my training to almost exclusively calisthenics. This wasn’t because it was “better” or any more worthy than weightlifting, but simply because I was excited. Deep in my heart, I wanted to master that muscle up, and that would take time. Nothing comes easy and I needed to devote effort to this cause, so I allocated more time to bodyweight training, which left less time for weights.

Training for Longevity

We train to be fitter and stronger and to navigate through this life with greater vitality and longevity. Training the muscle up and other street workout “money moves” made me feel more alive than I’d felt in a very long time. My passion for training was ignited all over again and I was on fire.

In the last eleven years since I first witnessed that muscle up, outdoor calisthenics has grown to an immense level of popularity. Although many consider this a “movement” (a word that gets thrown around a lot these days), I consider it a return to the basics. After all, bodyweight training has been around since the dawn of man, and precedes the invention of barbells, kettlebells, and isolation machines. Some people are profoundly inspired by this resurgence, as I was. Others are not and I get it. It’s easy to look at YouTube or Facebook and get bombarded with images of extreme calisthenics or seemingly impossible moves and simply write them off as party tricks. Well, they’re not.

In fact, the following five exercises are some of the most amazing demonstrations of strength and skill in the entire exercise kingdom. Each of these movements fuses power, mobility, and balance. Not only do they require great muscular recruitment, but they also demand a practical rehearsal of the movement patterns themselves. For that reason, it is important to be patient. Some are harder than they may appear, but like all exercises, they can be learned with discipline, hard work, and consistency. Anything can.

Furthermore, it is important to have a solid foundation in the basics before attempting these “money moves.” Make sure you’re up to snuff in your push ups, pull ups, squats, lunges, and dips. That’s where it begins. What follows is how far it can go. Enjoy the ride!

The 5 Street “Money Moves”: 1. The Muscle Up

As you know, this was the exercise that changed it all for me. Many people view the muscle up as a combination of a pull up and a dip, and while it does borrow from both, the muscle up is truly a unique exercise in its own right.

To perform a muscle up, hang from the bar with an overhand grip and your hands positioned slightly narrower than you would for a pull up. Lean back and pull the bar all the way down to your sternum. At the top of your pull, reach your chest over the bar and extend your arms. Unlike a strict pull up, the body does not travel straight up and down in a muscle up; it must maneuver around the bar in a different movement pattern. I recommend extending your legs in front of you as a counterweight to help you keep your balance during this transition. It will take some practice to get a feel for the timing. Respect the journey.

Muscle up

The 5 Street “Money Moves”: 2. The One Arm Push Up

The first time I and so many others from my generation saw a one arm push up, it was performed by Sylvester Stallone in the motion picture Rocky. This left an indelible mark on the Danny Kavadlo of yesteryear. Clearly, I’ve been working on this one a long time.

Start in a standard push up position, but with your feet further apart and your hands closer together. I recommend keeping your feet apart because this wider stance can help eliminate any wavering or “snaking” at the hips (which is virtually impossible to eliminate with your feet completely together). In other words, the body should be a moving plank.

Keep tension throughout your entire body and remove one hand from the floor, placing it at your side. Bend at the elbow and shoulder of your grounded arm and lower your chest toward the floor, making sure to keep your elbow close to your side. Pause briefly with your chest approximately one inch from the ground, then press yourself back to the top, maintaining tension in your abs, glutes, and legs the entire time. In time, you can even attempt one arm plyometric push ups like the Italian Stallion.

One arm push up

The 5 Street “Money Moves”: 3. The Pistol Squat

Even guys who can barbell back squat an enormous amount of weight can find the pistol squat to be extremely challenging, even humbling. I know I did. Because of the incredible amount of mobility and balance required for this exercise, even seasoned squatters need to proceed with caution.

Begin your pistol squat by standing upright and lift one leg forward in the air with your knee fully extended. Reach your arms in front of you and bend from the hip, knee, and ankle of your standing leg to squat down as low as possible. Pause when your hamstrings come in contact with your calf, keeping tension throughout your body, then return to the top position.


The 5 Street “Money Moves”: 4. The Human Flag

The human flag is perhaps the single most breathtaking visual in the street workout stratosphere. Picture it: A human being suspended horizontally in the air with no points of contact than only their two hands on a vertical object. Whoa.

Let’s give it a try.

Begin the human flag by placing your hands onto a vertical pole. They should be slightly wider than shoulder width apart. Keeping your bottom arm locked and your grip tight, kick up into a horizontal position with your body perpendicular to the pole. Brace every muscle in your body as you press with your bottom arm and pull with your top arm. Positioning your body at a slightly lower (or higher) angle and/or tucking one or both knees are good ways to train until you are capable of achieving the full expression of the human flag.

Human flag

The 5 Street “Money Moves”: 5. The Front Lever

The front lever is straight out of the school of “harder than it looks” exercises. When people first see it, they often don’t realize what it takes to properly execute it. I assure you, this beast takes some time to tame.

To perform a front lever, start out in an active hanging position, with your hands firmly gripped to a bar, your scapula retracted, and your shoulders packed. Make sure there is tension in your entire body. Keep your elbows locked and squeeze the bar tightly as you pull your body up until it is parallel to the ground. It can be helpful to envision driving the bar down toward your hips. Flex your lats, abs, glutes, and quadriceps in order to maintain a straight body. Hold this position, then lower yourself back down.

Front lever

Embrace the Challenge

Remember, my friends, you don’t have to be from the streets to practice. These exercises are for everybody who is ready for a unique physical challenge. Train hard and have fun. That’s what it’s all about—now go get that money!

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