How to Draw Lenny: Mastering the Art of Facial Illustration In Steps.

How to Draw Lenny

In the vast universe of internet emoticons, the Lenny Face stands out as an emblem of cheeky humor and digital culture. Characterized by its iconic smirk and playful asymmetry, “( ͡° ͜ʖ ͡°)” has transcended beyond mere characters on a screen, finding its way into the hearts of netizens worldwide. Whether you’ve stumbled upon it in an online chat, seen it emblazoned on merchandise, or simply heard of its legendary status, this guide is dedicated to diving deep into “How to Draw Lenny”? From its intriguing origins to the nuances of sketching its features, we’ll embark on a journey that celebrates the fusion of art, history, and digital expression.

1. Introduction: The Popularity and Origin of the Lenny Face

The “Lenny Face,” also known as “( ͡° ͜ʖ ͡°)”, is an emoticon that gained significant attention and use on the internet. This seemingly simple set of characters has captured the fascination of internet users, often employed to convey a sarcastic or cheeky mood.

Originating from a post on the Finnish image board Ylilauta in 2012, the Lenny Face quickly spread across various platforms, becoming a universal symbol of internet humor. The emoticon’s actual name, Lenny, came about as an affectionate nickname from the online communities that popularized it.

Draw Lenny

2. Understanding the Basic Elements of Lenny

Drawing the Lenny Face might seem straightforward, but each component has its distinctiveness that gives the emoticon its iconic appearance.

Eyes and Eyebrows: The eyes of Lenny are not symmetrical. The left eye, resembling a degree symbol (°), is smaller than the right eye, which often adds to its cheeky appearance. The eyebrows, situated above the eyes, give the face its mischievous expression.

Nose and Facial Structure: While some might overlook it, the simple “ʖ” character represents the nose and the upper lip. This is crucial as it positions the eyes and the mouth, providing a central point in the face.

The Signature Grinning Mouth: The Lenny’s face is widely recognized for its smirk. The mouth extends wider than most traditional emoticons, which imparts a sly or teasing demeanor.

3. Materials Needed for Drawing Lenny

Drawing the Lenny’s face can be an amusing exercise, whether you’re sketching it on paper or designing it digitally. Here’s what you’ll need for both methods:

  • For Traditional Drawing:
    • Sketchbook or Paper: Preferably a clean sheet without lines to ensure your drawing isn’t skewed.
    • Pencil: For initial sketches. It’s best to start light and later define the lines.
    • Eraser: For correcting mistakes or refining your drawing.
    • Ink Pen or Marker: To outline your final design and make it pop.
  • For Digital Drawing:
    • Tablet or Computer: A device equipped with a touchscreen can be especially handy, but a mouse can work too.
    • Graphic Software: Programs like Adobe Illustrator, GIMP, or even Microsoft Paint can suffice, depending on your familiarity and the level of detail you desire.
    • Digital Stylus (Optional): For those wanting more precision in their digital art.

With these tools in hand, you’re ready to bring the mischievous Lenny Face to life!

4. Step-by-Step: How to Draw Lenny

Drawing the Lenny Face is an exercise in attention to detail, as it’s the subtle variations in each character that give Lenny its unique expression. Here’s a breakdown:

Starting with the Eyes:

  1. Begin by drawing the left eye as a small circle, reminiscent of the degree symbol (°).
  2. For the right eye, make a slightly larger circle. The asymmetry between the two eyes adds to Lenny’s cheeky demeanor.

Sketching the Nose:

  1. Directly between and slightly below the eyes, draw a small curve that resembles the upper lip.
  2. Just above this curve, indicate the nose with an inverted U-shape. This simple representation is reminiscent of the “ʖ” character.

Perfecting the Grin:

  1. Start by drawing a curved line that extends wider than the width between the eyes. The broader smirk gives Lenny its teasing look.
  2. Slightly tilt the ends of the mouth upwards. This adds an extra touch of mischievousness to the face.

5. Variations of the Lenny Face

As with many internet sensations, the Lenny Face has seen various adaptations over the years. While the original “( ͡° ͜ʖ ͡°)” remains iconic, there are several creative versions that add to its rich tapestry.

Lenny’s Many Expressions: From the flirty Lenny “( ͡~ ͜ʖ ͡°)” to the shocked Lenny “( ͡o ͜ʖ ͡o)”, there’s a version for nearly every emotion.

Famous Memetic Adaptations: Some variations integrate popular meme elements, such as wearing sunglasses or donning a wizard hat. These adaptations often emerge from trending internet jokes or events.

6. Tips for Perfecting Your Lenny Sketch

Achieving a perfect Lenny drawing might require some practice, especially if you’re aiming to capture its specific cheeky essence. Here are some pointers:

  • Correcting Common Mistakes: One common mistake is making both eyes symmetrical. Remember, the charm of Lenny lies in the subtle asymmetry of its features.
  • Adding Personal Flair and Style: While staying true to Lenny’s core design, don’t hesitate to incorporate personal touches, such as additional facial features or accessories, to make it uniquely yours.
  • Practice Makes Perfect: Drawing Lenny multiple times can help familiarize you with its components, making it easier to recreate or adapt in the future.

With these instructions and tips, you’re on your way to mastering the art of drawing the iconic Lenny Face!

7. Digital Drawing: Bringing Lenny into the Digital Age

While the Lenny Face emerged from the realm of digital text characters, translating it into a digital art piece offers a unique fusion of classic emoticon charm and modern artistic techniques.

  • Tools and Software Recommendations:
    1. Adobe Photoshop: Ideal for detailed digital paintings and nuanced brushwork.
    2. Adobe Illustrator: Perfect for vector-based renditions of Lenny, allowing for scalable art without loss of quality.
    3. GIMP: A free, open-source alternative with a variety of tools similar to Photoshop.
    4. Procreate: For iPad users, this app offers a natural drawing experience with a digital touch.
  • Digital Shading and Coloring Techniques:
    1. Layering: Use multiple layers to separate different elements of Lenny, such as eyes, nose, and mouth. This makes editing and shading easier.
    2. Brush Selection: Opt for soft brushes for smooth gradients and hard brushes for defining sharp edges.
    3. Color Picking: While the classic Lenny is monochrome, playing with colors can offer a vibrant twist.

8. The Cultural Impact of the Lenny Face

The Lenny Face, despite its simplicity, has left a lasting mark on internet culture and beyond.

  • Lenny in Pop Culture: Beyond forums and chat rooms, Lenny has made appearances on t-shirts, stickers, and even in some unexpected places like TV shows and music videos as a nod to internet-savvy audiences.
  • The Internet Meme Evolution: Lenny’s rise and persistence offer insights into the lifecycle of Internet memes. Unlike many digital trends that fade quickly, Lenny has demonstrated remarkable staying power, morphing and adapting with the times.

9. Conclusion: Embracing the Fun of Drawing Lenny

Drawing the Lenny Face, whether traditionally or digitally, offers an opportunity to connect with a piece of internet history. As an embodiment of online humor and culture, mastering the art of drawing Lenny can be both a fun pastime and a nod to the evolving landscape of digital expression. Whether you’re sketching for personal enjoyment or showcasing your renditions online, Lenny’s iconic smirk serves as a reminder of the internet’s whimsical and ever-changing nature.


What is the Lenny Face?

The Lenny Face denoted as “( ͡° ͜ʖ ͡°)”, is a popular internet emoticon used to convey a cheeky or sarcastic mood, originating from a Finnish image board in 2012.

How did the Lenny Face get its name?

Yes, there are numerous variations of the Lenny Face, each depicting different emotions, from flirtatious to shocked, as well as memetic adaptations.

Can I draw the Lenny Face both on paper and digitally?

Absolutely! The Lenny Face can be sketched traditionally on paper or designed digitally using various software like Adobe Illustrator, Photoshop, GIMP, or Procreate.

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