“There’s an old saying about those who forget history. I don’t remember it, but it’s good".— Stephen Colbert
Stephen Colbert may have gotten his start on The Daily Show as a correspondent, but he truly came into his own as the host of The Colbert Report by—ironically—playing a character that is nothing like him. He helped bring humor to the world of politics but did it in a way where he was teaching and not just ridiculing, and his success managed to bring him to the coveted late night post held by David Letterman for decades. Everything about the host Colbert may not be true, but all of these facts about the real-life Colbert are!
1. Hate The Player, Not The Game
Stephen Colbert is best known for his portrayal of the character... Stephen Colbert, which he played on both The Daily Show and on his hit spinoff The Colbert Report. It’s important to note that he is far from the egotistical, Republican, political pundit he played for almost 10 years. He’s actually a registered Democrat and a super nice guy.
2. The Student Becomes The Teacher
It’s surprising that they didn’t change the name of the Emmy award for Best Variety Show to the Jon Stewart Award, as he won it for The Daily Show ten years in a row! That is, until Stewart’s apprentice Colbert ended the streak by taking home the award in 2013 for The Colbert Report.
3. Split In Two
The Colbert Report would go on to win the Emmy again the following year and would hold the honor of being the last show to ever win the award. The Television Academy decided to turn the Variety Series category into two awards, Outstanding Variety Talk and Outstanding Variety Sketch. Colbert may not have won as many Emmys as Stewart, but at least he got the last laugh!
4. Comedy Training
Colbert got his start in comedy at the famous Second City improv theatre in Chicago, Illinois, where he would hone his skills on the stage and on the road, meeting several friends and future collaborators.
5. Grunt Work
Colbert actually started off as an employee with Second City and not a performer, as his top priority at the time was money and a job. It wasn’t until he found out that employees get free classes that he decided to take a few, and the rest is history. 
Eugene Powers, Shutterstock
6. Birth Control
To say Colbert has a big family would be an understatement; Colbert is the youngest of 11 kids, consisting of eight boys and three girls.
7. Call Me ColberT
Apparently, everyone has been pronouncing Colbert’s name wrong, even Colbert himself. The “t” isn’t supposed to be silent, and should be pronounced Cole-bert. He always wanted to pronounce it without the “t" though, and decided to do it after he got a second opinion from an astronaut he met while on a flight, who agreed it was the right call. And that's why it was the "Colbear Repore," not the Colbert Report.
8. Well Met, Young Stephen!
Colbert was a huge fan of Dungeons & Dragons as a kid, playing non-stop from 1977 until 1981. Although he didn’t realize it at the time, he’s since noticed that the role-playing and improvisation of the game helped him later on in life and in his career.
9. Risky Business
In 2006, Colbert delivered what stills stands today as the most controversial and divisive White House Correspondents Dinner speech ever. While in character, Colbert continuously insulted then-President George W. Bush in a way that sounded like he was complimenting him, all while standing just feet away from the man. It was considered either hilarious and fearless or pathetic and rude, depending on which political party you talked to.
10. What’s Your Major?
Colbert originally attended Hampden-Sydney College of Virginia to major in philosophy, but couldn’t shake the acting bug and later transferred to Northwestern University to study theatre.
11. Collaboration
Colbert met longtime collaborators Amy Sedaris and Paul Dinello during his time at Second City, and would later go on to create and star with them in two short-lived TV shows, Exit 57 and Strangers with Candy, eventually getting to make a Strangers with Candy movie made as well.
12. Small World
Colbert and his wife, fellow actor Evelyn McGee, have been married since 1993. They both grew up in the same town in South Carolina—in fact, when they were kids, they lived just blocks away from each other, but they had no idea and didn't meet until much later in life when they were both adults.
13. Love At First Sight
Colbert and McGee met at the opera back when Colbert was trying to decide whether or not he should marry a different woman he was in a relationship with at the time. In the end, he knew that night he wanted to get married, but to McGee, and it seems like he made the right call.
14. TV Raised Me
Colbert and McGee have three children together, a daughter, Madeline, and two sons, Peter and John. Colbert describes his parenting style as “Go watch the TV,” something he picked up from his mom, who had 11 kids to deal with, so her time was sparse.
15. Kids Just Don’t Understand
When it came to watching TV, however, Colbert did enforce one rule on his kids. They weren’t allowed to watch The Colbert Report. Colbert believes that kids don’t understand sarcasm and was worried that his kids wouldn’t understand he was playing a character on TV.
16. Behind The Scenes
Colbert auditioned to be a cast member on Saturday Night Livej but ultimately didn’t make the cut. However, he did end up getting hired as a writer on the show a few years later, and even found his way on screen in minor roles for a few sketches. His greatest contribution to the show was probably when he and Steve Carrell were the voices of the "Ambiguously Gay Duo".
17. Missed Opportunity
Speaking of SNL, remember that time Colbert hosted? You probably can’t, because it never happened. Whether by choice or simply because he was never asked, Colbert has yet to host the sketch show, and unless he drops his Late Show hosting duties, it may never happen.
18. When We First Met
During his time at Second City, Colbert was Steve Carrell's understudy. The two would go on to work together on The Dana Carvey Show and The Daily Show and remain great friends to this day. Even Stevphen lives!
19. No Love Lost, Eh?
Colbert (the character at least) has a weird beef with Windsor, Ontario, once referring to the city as the worst place on Earth on The Colbert Report. He then followed it up by questioning if Windsor was the Earth’s lowest point , in his book America Again: Re-becoming the Greatness We Never Weren’t. He defended that comment by claiming it was a question and stating that for all he knows the lowest point could be in Winnipeg. Good save!
20. Hidden Talent
Before taking over as host of The Late Show, Colbert appeared as a guest back in the Letterman days and performed a trick for the audience. It’s a skill he claims to have had since he was a kid, where he folds his ear inside out—not the trick—and then winks to pop it back into place. It’s probably best seeing it for yourself on YouTube.
Wikimedia Commons, Chairman of the Joint Chiefs of Staff
21. Fluent In Elf
Colbert can speak more than one language if you count the fictional language of Quenya—spoken by elves in Lord of the Rings—as one of them. He is reportedly fluid in the tongue, which must come in handy almost never.
22. TV, Is There Anything It Can’t Do?
Colbert was worried as a kid that people would think he was stupid because of his Southern accent, which was something he noticed was associated with Southern characters on TV shows. So, he used TV to help get rid of the accent, by copying the way that news anchors talked.
Wikimedia Commons, David Shankbone
23. What Could Have Been
As a child, Colbert had dreams of becoming a marine biologist, but an operation to fix a perforated eardrum ended up causing even more damage and left him deaf in his right ear. Because of this injury, Colbert can't scuba dive, which ended his chances at pursuing a career in marine biology. I'm all for saving the whales, but I'm glad he ended up in comedy.
s_bukley, Shutterstock
24. Every Six Years
Colbert has appeared twice on Time’s 100 Most Influential People list, in 2006 and 2012, and if the pattern continues, expect to see him pop up again this year!
Wikimedia Commons, Montclair Film
25. Number One In My Books
In 2007, Colbert added New York Time’s Best Selling author to his long list of accomplishments, after the release of his book I Am America (And So Can You!) reached number one on the list.
26. Part Of The Team
Colbert helped the US Speed Skating team raise enough money to compete in the 2010 Winter Olympics after a key sponsor dropped out. Colbert urged his viewers to pledge money to the team, which led to over 9,700 viewers donating over $300,000 dollars! To advertise the sponsorship, Colbert wanted his face on the skaters’ uniforms, but settled for the Colbert Nation logo instead.
27. Dearly Beloved
Colbert is an ordained minister with the Universal Life Church. He even used the power vested in him to marry real-life couple Mike Cassesso and MaiLien Le live on an episode of The Colbert Report.
Ron Adar, Shutterstock
28. God’s Favorite Teacher
Colbert used to teach Sunday school at the church he attends in New Jersey. He was apparently a bit unorthodox in his teaching methods, as he would sing songs and play games with the students.
Wikimedia Commons, Dwight Burdette
29. Channel Surfing
In 2015, the residents of Monroe, Michigan, or at least the ones who watch public access TV, were in for a fun surprise when they turned on Only in Monroe to see Colbert on their screens. He played a TV host and interviewed rapper Eminem in a painfully awkward, but hilarious, segment.
30. Wake Me Up When The Show Starts
Colbert took method acting to a whole new level when he purposely fell asleep on stage during a sketch at Second City. For some reason, it was a goal of his to do this, and all it took was some jetlag and dim lights before the start of the show for him to pass out cold!
Jaguar PS, Shutterstock
31. Student Of The Game
Colbert was a fan of comedy as a kid, and had a large collection of comedy albums, with his favorite ones coming from comedians Bill Cosby, George Carlin and Dean Martin.
32. Misery Loves Comedy
Colbert may have been a fan of comedy as a kid, but he never had any intention of pursuing it as a career. He did want to act, but his original plan was to become “a serious actor with a beard who wore a lot of black and wanted to share his misery with you". It didn’t take long, however, for him to find his true calling in life, and here we are today.
33. I Was Here First
Colbert actually predates Jon Stewart on The Daily Show, serving as a correspondent on the show with original host Craig Kilborn. However, Colbert credits Stewart’s involvement later on as the reason why he came to love political humor and comedy.
34. Before Late Nights There Were Early Mornings
Colbert may best known for his stint as a correspondent on The Daily Show, but he actually got started as a correspondent on another, less irreverent, show. Desperate for cash, Colbert agreed to appear on Good Morning America and filmed two reports, but only one made it to air.
35. First Tier Is Here For You
A lot of actors got their start in commercials, and Colbert is no different. One of his first acting gigs was in a commercial for First Tier Bank, and it can be described with the same word that most famous actors' first commercials can—cheesy.
Kathy Hutchins, Shutterstock
36. Experts Only
Colbert put his Second City training to the ultimate test when he appeared on the popular improvisational comedy show Whose Line Is It Anyway? in 1999 and then again in 2006.
37. Keep It In The Family
Colbert’s wife once played his mom in an episode of Strangers With Candy. Even though they were acting, that must have felt pretty darn weird to write.
38. Never Forget
September 11, 1974, is a day Colbert and his family will never forget, as his dad and two of his brothers—Peter and Paul—lot their lives in a plane crash. The event would have a major impact on Colbert and shape him into the man he would become later on in life.
39. Escapism
After passing of his father and brothers, Colbert became obsessed with books and the fantasy world, most notably Middle Earth and the Lord of the Rings.
40. Fantasy Becomes Reality
Director Peter Jackson caught wind of Colbert’s love and deep knowledge of the Lord of the Rings mythology and decided to make his dream a reality by giving him a cameo in The Hobbit: The Desolation of Smaug. Colbert was credited as the Laketown spy.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27
