John Stewart--he has the ability to maintain his liberal perspectives while not falling off the cliff completely and becoming a Bernie Sanders-esque catch phrase garden gnome sitting on somebody's lawn, yelling a recorded snippet of the latest radical liberal cause.
Bill Maher--he just has a way of cutting through the bullshit on certain issues. I don't agree with him on a lot of things but I do appreciate his willingness to acknowledge the issues with Islam world wide as well as the way he called out our PC culture in a recent monologue after Trump was elected.
Heidi Heitkamp--she's one of North Dakota's Senators and she has a long history of actually getting shit done in politics because of her willingness to cross party lines and stand firmly on certain issues that are important to North Dakotans. Quite frankly, I just have a great deal of respect for her and hope she's a Senator until she wants to retire.
Sarah Silverman--I really don't find her all that funny, but recently I appreciated something she did as a part of her I Love You, America series. She actively and firmly stated that after diving into the belly of the beast and meeting Trump voters, she came to realize that she quite liked many of those people, and that perhaps there are fewer things that divide us than we realize. In our day and age where celebrities have a great deal of pull, it was very important to me that a liberal personality acknowledged that all Trump voters aren't Lucifer in the flesh.
Canadian Psychologist Jordan Peterson. He vehemently defended free speech in the wake of Canadian bill C-16, which mandated compelled usage of all the made up gender pronouns (Xe and Xer and other dumb shit like that), and refusal to do so constituted hate speech lolololol. If we think we're fucked up from a political correctness standpoint, Canada is twice as bad.
Also look up the Lindsay Shepherd controversy in regard to Peterson
Mike Rowe--I don't know for sure whether he's conservative on social issues, but Rowe has stood firmly behind the fact that there are jobs available in this country, good jobs that people are actively choosing not to pursue. It seems his purpose as a political personality is to break down stupidity. Recently somebody attacked him claiming he was "anti-education" and "anti-science" and he just eviscerated the dumb bitch in his response, literally proving her attack wrong with ease. I love that he responds to people, too. Rowe has a humility about him that is easy to connect with, and he just seems like a regular dude, and he pulls it off with ease.
Ben Shapiro--whatever you feel about his stances on transgenderism and gender dysphoria, Shapiro firmly believes in his conservative values and he can absolutely destroy just about anybody in a debate. The guy is flat out brilliant, and I have a tendency to gravitate toward individuals who are willing to stand behind unpopular opinions and are able to both, a. cite sources and b. constructively and respectfully debate those issues with people who disagree with them. Shapiro will engage in debates without resorting to personal insults, which quite often get thrown back at him, and yet he repeatedly gets called morally corrupt and indecent. It's utterly confusing.
Tomi Lahren--I can't count on two hands the issues I disagree with her on, but she absolutely represents middle America in her Final Thoughts segments and every now and then she takes on an issue that is hurting small businesses or farmers and lays waste to the causes of said issue, most notably restrictions placed on locally raised beef over the past 5 years which had crippled the market and made it nearly impossible to make money tenably on a ranch that isn't massive. While I often find her rants to be childish and flat-out wrong, I can't help but appreciate when she does strike gold because it's often something that is affecting everyday Americans.
Joe Rogan--Rogan is so unbelievably comfortable in his own skin, and his ability to stand by his beliefs and debate respectfully with others say a great deal about his character. It's easy to find yourself agreeing with Rogan, but when you do disagree, the way he presents his point of view almost prevents you from having a negative reaction to him, himself. His podcast is phenomenal and something we all should be listening to in order to as a part of developing our political opinions as well study his demeanor in debate and heated moments, because he does a great job of remaining respectful for the most part.