Andy Samberg Explains "Slightly Embarrassing" Origins of SNL's "Like a Boss" Short
The 2009 song almost didn't get a video, but then it became an unexpected hit.
If you were looking for a succinct way to describe the second half of the early 2000s, might we suggest "The Boss Moment?"
The June 17, 2025 episode of The Lonely Island and Seth Meyers Podcast revisited the Digital Short "Like a Boss," which aired on Saturday Night Live in Season 34. As Andy Samberg explained on the pod, it was hard to avoid songs about being the boss in 2009.
"The one we listened to most was when we were shooting Hot Rod. We listened to Rick Ross' first album, Port of Miami," he remembered, referring to The Lonely Island's 2007 feature film. "We shared a trailer, and we would blast that. There's a song on that album called "Boss."
In fact, Rick Ross alone had songs titled "Boss," "The Boss," "You the Boss," and "Ima Boss."
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The Lonely Island's "Like a Boss" parodied Rick Ross and Slim Thug
"The Rick Ross ones, I think, musically influenced it the most, but it was a boss moment, Seth," Samberg explained to his co-host. "It was a moment where a lot of people were saying, 'I'm the boss,' 'I am like a boss.'"
Akiva Schaffer added that the Lonely Island's "Like a Boss" is actually a direct parody of rapper Slim Thug's 2004 song "Like a Boss," and said that the group used to joke about taking the word "boss" literally, picturing a boss in an office instead of a cool guy in a luxury car.
"It's slightly embarrassing because it's so basic," Samberg admitted. "It was one of the days where I was in the stud[io], and I started just writing it and I was like, 'What if the boss was like a boss at an office, isn't that funny?'"
By the time Samberg brought Schaffer in, he'd written the first chunk of the song.
"We thought it was going to be sort of like a filler track," said Samberg.
"Almost like an interlude," added Schaffer. "Because the premise is so first-thought. But it shows how execution is everything."
Watch the "Like a Boss" Digital Short above, and listen to the full episode of The Lonely Island and Seth Meyers podcast below.
Andy Samberg and Seth Rogen star in the twisted "Like a Boss" video
The short starts with Rogen's character sitting down with Samberg's character to give him a performance review. Asking Samberg to walk him through a typical day at work as "the boss," Rogen hears about what starts out like a pretty normal office day, then turns into something of a nightmare.
Samberg said that they had no plans to make "Like a Boss" into a video, but the song had been released on their 2009 album Incredibad, and it was quite popular in certain circles.
"The label told us, and I believe the quote was like, 'The kids around the office really like that one,'" he said. "Like, 'Some of the guys at their cubicles that have the record and are helping put it together have been pointing out that they really like this song,' and that turned us around on it."
The song and video became much more popular than the group anticipated.
"It's one of our bigger singles for sure," said The Lonely Island's Jorma Taccone.
The first half of the video features both SNL cast members and writers, including Paula Pell and John Mulaney, working in the office as Samberg's character slowly loses his mind. See if you can spot in the lyrics where things take a real turn.
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"Like a Boss" lyrics by The Lonely Island
Talk to to corporate (like a boss)
Approve memos (like a boss)
Lead a workshop (like a boss)
Remember birthdays (like a boss)
Direct work flow (like a boss)
My own bathroom (like a boss)
Micromanage (like a boss)
Promote Synergy (like a boss)
Hit on Debra (like a boss)
Get rejected (like a boss)
Swallow sadness (like a boss)
Send some faxes (like a boss)
Call a sex line (like a boss)
Cry deeply (like a boss)
Demand a refund (like a boss)
Eat a bagel (like a boss)
Harassment lawsuit (like a boss)
No promotion (like a boss)
Fifth of vodka (like a boss)
S--- on Debra's desk (like a boss)
Buy a gun (like a boss)
In my mouth (like a boss)
Oh f--- man I can't fucking do it, s---!
Pussy out (like a boss)
Puke on Debra's desk (like a boss)
Jump out the window (like a boss)
Suck a dude's d--k (like a boss)
Score some coke (like a boss)
Crash my car (like a boss)
Suck my own d--k (like a boss)
Eat some chicken strips (like a boss)
Chop my balls off (like a boss)
Black out in the sewer (like a boss)
Meet a giant fish (like a boss)
F--k its brains out (like a boss)
Turn into a jet (like a boss)
Bomb the Russians (like a boss)
Crash into the sun (like a boss)
Now I'm dead (like a boss)
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