Late night TV hosts are known for making fun of celebrities getting into trouble, but they've
also experienced their fair share of trouble themselves.
Here are some of the darkest and most scandalous moments in the off-screen lives of TV's greatest
talk show hosts.
Every night during his 16-year run as host of The Daily Show, Jon Stewart spoke truth
to power.
Perhaps he got a dry run for that dynamic though the simple act of changing his name.
Stewart's father is a physics professor named Donald Leibowitz who left the family when
the future comedian was just 9 years old.
That and the divorce that followed left Stewart with what he's described as a "complicated"
relationship with his father.
"It was incredibly, uh, disorienting."
Their relationship was so complicated, in fact, that when Stewart entered show business,
he dropped his father's last name completely, as Jonathan Stuart Leibowitz became Jon Stewart.
He nearly made an even more pointed gesture.
As he told The Guardian in 2015,
"There was a thought of using my mother's maiden name, but I thought that would be just
too big a f--- you to my dad."
One reason Stewart's been open with that story is because he's received criticism from people
who think he dropped his original name to conceal his Jewish heritage, but he's made
sure to note,
"I hate myself for a lot of reasons, but not because I'm Jewish."
Losing a family member to a random tragedy is among the worst things that can happen
to a person.
It's nearly impossible to imagine what it's like to lose multiple loved ones, all at once,
to the same horrible fate.
Sadly, this all happened to Stephen Colbert in 1974.
He was just ten years old at the time, the youngest in a family of 11 kids living in
Charleston, South Carolina.
His father, James, and two of his older brothers, 15-year-old Peter and 18-year-old James, were
onboard Eastern Airlines Flight 212 when a pilot error caused the plane to crash in a
cornfield in North Carolina, killing all three.
All the other Colbert children were older and had moved out of the family home by then,
reducing the household to just Stephen and his mother.
This horrible event led Stephen to act out and struggle to graduate from high school.
As he got older, he learned to cope with the tragedy, and even how to use it in his burgeoning
comedy career, as he figured out a way to be fueled by the fear that lingered.
As he told GQ in 2015,
"Acceptance is not defeat.
Acceptance is just awareness."
"I finally had time to, sort of, I suppose be alone with the idea that they were gone."
"To process it."
"Yeah."
After the post-Johnny Carson late night wars settled, with Jay Leno hosting The Tonight
Show and David Letterman starting up the competing Late Show at CBS, Leno wound up looking like
the bad guy.
He was seen as a safe, mainstream comedian loved by network brass who took part in the
corporate machinations to get his dream job and throw his one-time friend Letterman under
the bus.
Other major players in late night openly savaged Leno.
Arsenio Hall, for one, told Entertainment Weekly,
"I always hear that Jay and I are friends when they interview him.
Jay and I are not friends."
Meanwhile, Dennis Miller told EW that he thought Leno and his team were aggressive careerists.
He also confessed,
"Jay and I were very good friends at one point.
I don’t think I’d talk to him again, nor would he want to talk to me."
Even Carson's former Tonight Show bandleader Doc Severinsen got in on the Leno-bashing,
telling USA Today,
"Jay Leno is running around trying to figure out, 'How can I get them to like me?'
Frankly, I haven't seen anything that makes me want to stay tuned in."
When Jon Stewart announced his intention to vacate the anchor chair on The Daily Show
in 2015, the media and fans speculated about who his successor would be.
But there was one big problem, as seemingly no high-profile comedian wanted the job.
Amy Poehler, Amy Schumer, and Chris Rock all turned down the gig.
So the show ultimately hired from within, giving the plum position to South African
comedian Trevor Noah, a correspondent who'd joined the show just a few months earlier.
While some wondered just who Noah was, others vetted him by scouring his social media history,
thereby uncovering a bunch of old, problematic tweets.
Some of them were jokes made at the expense of broad groups of people, including Israelis,
women, and overweight people.
After calls came for Comedy Central to rescind the job offer, Noah issued an apology, or
rather an explanation, by way of Twitter:
"To reduce my views to a handful of jokes that didn't land is not a true reflection
of my character, nor my evolution as a comedian."
After one year at the University of Nevada, Las Vegas, Jimmy Kimmel headed to Arizona
State University, where he got his first job in radio and met a classmate named Gina Maddy.
In short order, she became his girlfriend, and then his wife.
When they wed, Kimmel was only 20.
As he explained to Huffington Post in 2012,
"My mom was 19 when she got married, so it didn't seem unusual to me.
It seemed unusual to all my friends, but not to me."
Within just a few years, Kimmel had two kids, but was struggling to maintain a stable family
life, as he bounced around various radio stations in different cities.
Things seemed to look up when he landed a job at the influential Los Angeles station
KROQ.
Soon after that, he broke into TV as co-host of the Comedy Central game show Win Ben Stein's
Money.
His per-episode pay of $550 was too little to allow himself to quit his radio gig, though,
so he worked punishing days that stretched from dawn into nighttime.
His long absences from home put a lot of pressure on his family life, and when he added hosting
The Man Show to his routine, things started to crumble.
Kimmel and Maddy separated in 2002 and were officially divorced by 2003, the same year
that Jimmy Kimmel Live! debuted on ABC.
For someone who's been part of the showbiz machine for more than 25 years, Conan O'Brien's
life has been refreshingly scandal-free for the most part.
But there have been a couple of dark chapters in his life.
In particular, there was that time in 2010 when NBC fired him from The Tonight Show after
less than a year on the job, and then there was that time a priest stalked him.
Father David Ajemian of Boston, who claims to have attended Harvard University at the
same time as O'Brien, reportedly sent threatening letters to the comedian's home and workplace
for more than a year.
In one letter, he seemed to be unreasonably angry about not being able to get tickets
to a taping of one of O'Brien's shows.
As the letter stated,
"I'm told by some of those officious little usher people that you're overbooked.
Is this the way you treat your most dangerous fans?
You owe me big-time, pal.
I want a public confession before I even consider giving you absolution."
In another letter, Ajemian alluded to O'Brien having to one day dodge a bullet.
Police arrested Ajemian and charged him with stalking and harassment, and the Roman Catholic
Archdiocese of Boston placed him on leave.
In 1996, Stephanie Birkitt joined the staff of The Late Show with David Letterman as an
intern.
She went on to make 260 on-camera appearances on the show.
In February 2006, Birkitt and Letterman struck up a romantic relationship.
This was while she was living with CBS News Producer Robert Halderman and Letterman was
with his longtime partner Regina Lasko.
Halderman learned of the affair in December 2008 when he found Birkitt's diary, which
detailed the many torrid nights she'd spent with Letterman.
Birkitt promised Halderman she'd end the affair, and a few months later Letterman and Lasko
married.
But then in the summer of 2009, Halderman spotted the lovers canoodling again.
Halderman went on to make an interesting decision, as he wrote a treatment for a screenplay about
Letterman and his purported relationships with Late Show staffers.
Then Halderman snuck it into Letterman's car and told him that for $2 million, he'd keep
his mouth shut.
Otherwise, there would be consequences.
Since that qualifies as extortion, Letterman called authorities.
After Halderman tried to cash a fake $2 million check from Letterman, he was arrested.
On October 1, 2009, Letterman came clean on The Late Show, admitting that he had slept
with women who work on his show.
"There's a letter in the package, and it says that, uh, 'I know that you do some terrible,
terrible things.'"
Four days later, the New York Post revealed Birkitt's identity, and a few months later,
Halderman received a six-month prison sentence.
As of 2020, Letterman and Lasko remain married.
A little thing like marriage didn't stop Johnny Carson from dating.
The longtime Tonight Show host's lawyer and close friend Henry Bushkin detailed several
of Carson's extramarital escapades in his book entitled Johnny Carson.
This included an affair with a Playboy model, a clothes-free pool party on a Las Vegas rooftop,
and the time that one of his wives discovered a film of Carson in the act with a young woman.
"Those were the days that he and Ed McMahon were virtually out every night in New York
drinking.
Dark days in that sense."
But while Carson stepped out, he apparently didn't believe that his wives could as well.
Bushkin noted that Carson had proof that his second wife, Joanne, had quietly rented out
an apartment in New York City that he believed she used as a love nest.
Bushkin offered to file divorce papers, but Carson had a better idea.
He wanted Bushkin to accompany him and a security expert to break into that apartment, Watergate-style,
and find evidence of the tryst.
They successfully busted into the apartment and found what they were looking for.
Along with some men's clothes and lingerie, they noticed about six or seven framed photos
of Joanne's lover: NFL star Frank Gifford.
Bushkin revealed that when Carson realized his wife really was two-timing him, he leaned
against the wall and began to weep.
From 1973 to 1982, Tom Snyder hosted The Tomorrow Show, which aired right after The Tonight
Show.
Then from 1995 to 1999, he was the original host of The Late Late Show on CBS.
On both programs, he engaged in serious one-on-one chats with newsmakers and highbrow cultural
figures, and then veered off on long, rambling tangents.
His broadcasts were a brainy alternative to the typical comedic late-night shows.
In other words, he wasn't for everyone.
One person in particular who couldn't stand him was Johnny Carson.
According to Henry Bushkin's book Johnny Carson, the Tonight Show host believed that Snyder,
quote, "had no talent and was an officious bore."
One night in 1979, Carson took his inner circle out to dinner at a Hollywood hotspot and spotted
Snyder eating by himself.
Nobody in Carson's group invited Snyder over to their table, since they all knew that Carson
hated the guy.
Instead, Carson downed multiple glasses of wine, and glowered at Snyder.
Carson even eventually blurted out,
"Why the f--- is he staring at me?
I'm going to go over there and kick the s--- out of that guy."
So Carson went over there, and while Snyder tried to buy him a drink, Carson lunged across
the table and tried to grab Snyder's throat.
He couldn't quite reach, though, and Carson's sidekick Ed McMahon broke up the scuffle.
Craig Kilborn enjoyed a meteoric rise to the top of the talk show heap in the 90s.
As the original host of The Daily Show, his sarcastic edge got him noticed by CBS, who
installed him as host of The Late Late Show in 1999.
He went on to run a loose, silly show, but he walked away from the gig in 2004 after
just five years.
Afterwards, Kilborn virtually disappeared from showbiz, apart from a handful of small
roles.
A talk show comeback in 2010 called The Kilborn File lasted only a few weeks.
So what exactly happened to him?
As Kilborn explained to the Los Angeles Times in 2010,
"I didn't leave to do anything else, I left to leave."
He also indicated that he knew well before 2004 that he didn't want to host a late night
talk show anymore, adding,
"I thought late night was crowded, the formats repetitive.
I achieved my goals, and it wasn't all it was cracked up to be."
A Late Late Show producer agreed, telling the Times that in his position at CBS, Kilborn
was, quote, "totally bored."
"I say I lost interest in the comedy of late night.
I got bored of the comedy of late night."
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