The Best Observational Comedians for Live Events in 2020

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Written by Tim Grable

November 4, 2017

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The Best Observational Comedians for Live Events

Do you know what the tastiest type of comedy is? The one that analyzes insightful observations of our everyday lives. 

The best observational comedians know that observational humor never gets old. Since it stems directly from situations or people we’ve all come across in life, it hits the funny-bone in a very personal way. Trust me, we can all relate. We have all been there. That is the key to joy in this humor. Let us sample some of the silly subjects, shall we? Why do we all fail to find that one missing sock? Why does hair linger in the strangest places? Why does everyone’s boss seem to be drinking the same crazy Kool-aid? The observational comedians answer these mysterious questions in hilarious fashion. Whether you are young or old, from this country, or another – it does not matter. Spend time with their comedy material, and you are sure to hit the floor rolling, both at what they say and in how it reminds you of yourself.

Book The  Best Observational Comedians

When looking for entertainment for your next party or corporate event, you may be overwhelmed by the options presented to you. Every type of performer is available if you look hard enough, and you may be wondering which would suit your particular function the best, ensuring everyone in the group will have an enjoyable time. Consider the art of observational comedy; the heart of many stand-up comic’s routines, this style focuses on poking fun at the mundane elements of our lives, touching on aspects or experiences that the entire audience can relate to in a fresh and new way. Not only does everyone love comedy, but people are particularly taken with humor that applies to their everyday life and means something to them. It is sure to be a hit!

Daren Streblow

If you’ve ever raised a child or been in the vicinity of one who has just discovered their ability to communicate with words, you can undoubtedly understand where Daren is coming from in this bit. Who has not been in a grocery store and heard a small child shout while their parents tried everything to quiet them?  Call him the clean comic, the corporate comic, the Clean comedian – he suits all crowds, just don’t forget to book Daren Streblow funny as well. He avoids the sex-talk staples of other stand-ups but replaces it with much funnier jokes that we can all relate to and remember. Both corporate and non-profit groups welcome his relate-able style of humor.

Jeff Allen

Jeff Allen knows the kind of situational humor we are talking about here, folks. His witty sarcasm meets everyday life, and the audiences eat it up big-time. He takes to task the nutty trial’s of love and marriage, household-cleaning, 1960’s-style thinking, jogging, and (of course) parenting. He knows the humor and believe me, you know what he is talking about.

Michael Joiner

Michael Joiner smoothly makes this list of best observational comedians because his comedy is just that smooth. He started as a photo double for Bruce Willis but now he is writing, directing and improving all over the place. Making it through the recession, road construction, old folks, fast-lane driving – he smoothly delivers the laughs on all of it and then some.

Leanne Morgan

Don’t put Leanne in a corner when it comes to lifestyle humor – because she’ll fight her way out delivering one stunning punchline after another! Mrs. Morgan gets the job done with a wide-range of subjects. Summer camp, traveling, food, diet, health, wellness, and more – she delivers knock-outs on just about every topic.

Taylor Mason

Taylor Mason provides a unique and eclectic style of joke telling, sometimes with his routine set to music! His ability to pull the specific city and street names dear to his audience makes him instantly relatable, and the pointed discussion of bicyclists in winter is exemplary of the definition of observational comedy.

Henry Cho

There may not be a woman alive who has not been out for an evening on the town when she is approached by the very guy that Henry is describing in this routine. His illustration of the insecurity of some men in social situations reflects the difficulty of dating, which hits close to home for many an audience member.

Thor Ramsey

Possibly the perfect bit for the rapidly approaching wedding season, Thor Ramsey provides his brand of observational comedy mixed with a dash of physical comedy as well. The result is both hysterical and instantly relatable, a winning combination that is not to be missed by the crowd at any event.

Carlos Oscar

Differences in languages impact our ability to communicate effectively every day, and although it may not reflect on the individual, it can be both frustrating and (in the case of Carlos) endlessly funny. If you’ve ever been in a situation where you could not understand the person you were trying to talk to, you will undoubtedly relate to this routine.  Who knew that the comedy shared in Latino households was so very true-to-us-all and universal? Carlos Oscar knew; that is who! He ends up feeling like a member of the family once he gets done with his set. Airports, electronics, debt, family, the children, a wife – he “observes” it all – so you do not have to.

Rex Havens

Rex is a former college professor of business and law. Not only that, but he also was an attorney for a Fortune 500 company. All of this happened in the ’70s.  The transition to the stand-up comedy stage occurred in the ’80s. He always believed that laughter is the best defense that people can have in this confusing world.

Rex has a natural gift for entertainment, and so, in 1991, he left behind his career as a college professor for good.  His unique and hilarious take on marriage and family brought him much success. He managed to perform in all 50 states and around the world, in London, Amsterdam or Rome.  Rex’s stand-up comedy is family-friendly and appropriate for all ages.

How would you feel about having an observational comedian at one of your events?

Laughter is something that is loved universally, and observational comedy is one that transcends differences in opinion and lifestyle, one that rings true to all and brings together even the most diverse groups of people. As such, it is the perfect selection for any event you are planning and is sure to leave your guests wanting more.  You already laugh about this stuff in your life; you are already poised to feel the comic’s “pain,” energy, attitude, or words of bittersweet. Because you’ve been there yourself! Your friends, coworkers, life’s little foibles – it is all there. It is all LOL! Seek out or book up some of today’s best observational comedians, and you’ll be left in the midst of a laugh riot.

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