We could listen to these Lonely Island classics all night long! Welcome to WatchMojo and today we’re counting down our picks for the funniest, most memorable songs by the legendary trio that is Andy Samberg, Akiva Schaffer, and Jorma Taccone.
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00:00You can't hug a rolling stone, cause it'll crush you.
00:02Begging me to hug you again, that's when I shush you.
00:05Welcome to WatchMojo, and today we're counting down our picks for the funniest, most memorable songs
00:11by the legendary trio that is Andy Samberg, Akiva Schaffer, and Jorma Ticconi, The Lonely Island.
00:16Two chicks at the dance hall, take it to the dance hall.
00:19Trade these beads for their bra.
00:23Number 20, Sushi Glory Hole.
00:26Gentlemen, what do you have for us today?
00:29This.
00:30Hear us out.
00:30This ridiculous 2024 jam is an instant classic.
00:34Following up on Lorne Michaels' promise that Saturday Night Live's 50th season would be
00:38chock-full of surprises that honored the show's history,
00:41Sushi Glory Hole momentarily teleported fans back to the group's heyday.
00:45Sushi Glory Hole, imagine that.
00:50Sushi Glory Hole, imagine that.
00:52Instead of strange dick, you be getting a snack.
00:54A bonafide old-school SNL digital short,
00:57this instantly recognizable Lonely Island number finds Andy Samberg and Akiva Schaffer
01:01pitching Maya Rudolph, Kenan Thompson, and Bowen Yang an admittedly questionable culinary experience.
01:16While the group's trademark absurdist style is in full effect,
01:19we can't help but draw attention to Samberg and Schaffer's admittedly impressive flows.
01:24If only they weren't rapping about, you know, a friggin' Sushi Glory Hole.
01:38Number 19, YOLO, featuring Adam Levine and Kendrick Lamar.
01:42Judging by the comments on our last Lonely Island list,
01:45we really messed up by not including this cautionary anthem.
01:48Honestly, we can't argue with that.
01:50A song that includes this many warnings against everyday occurrences really makes you think.
02:13This paranoid pop-rap jam speaks to the trio's ability to satirize pop music with real bite.
02:18And that's not just a reference to featured guest Adam Levine's suggestion
02:22that listeners pull out all of their teeth.
02:35Be sure to look out for Kendrick Lamar's verse,
02:39in which the Lonely Island found the funniest possible way to use the future Pulitzer Prize winner.
02:44Instead of a typically dynamic verse about living it up,
02:47we get painfully mundane financial advice.
02:50Thanks, we guess?
03:03Number 18, The Creep, featuring Nicki Minaj.
03:09This is another fan-favorite according to our own comments section,
03:17and we can certainly see its slimy appeal.
03:20Released in January 2011, The Creep parodies dance trends in hip-hop
03:24that were popular at the time by adding a John Waters-themed twist
03:27down to the gray suits and pencil mustaches.
03:30Now pull your waistband up like you expecting a flood
03:33and stick your head down flat like it was covered in mud.
03:37Sandberg, Shaffer, and Ticoni almost make being a peeping Tom sound cool.
03:41Much like YOLO, a big chunk of the fun comes from an extremely game
03:45Nicki Minaj's legitimately great guest verse.
03:55She's so well-matched with The Lonely Island
03:57that we're surprised they haven't collaborated again since.
04:00Once again, the trio takes hip-hop and runs with it.
04:04We have never been so hyped to be creeped out before.
04:15Number 17, Incredible Thoughts, featuring Michael Bolton and Mr. Fish.
04:28The climactic scene of The Lonely Island's 2016 pop music mockumentary pop star
04:35features this profoundly intellectual track,
04:37the result of a legendary jam session between the reunited Style Boys,
04:41played by the group's members.
04:43In a scene that seemingly pays homage to the 2013 NSYNC reunion
04:47at the 2013 MTV Video Music Awards,
04:50Connor, Lawrence, and Owen unveil a brand new song
04:52that reveals their machinations of their so-called incredible minds.
04:57The song is a hilariously ridiculous mashup of preposterous one-liners,
05:11all anchored by special guest Michael Bolton's big sexy hook.
05:23Wait a minute, who was under that fish costume?
05:28That was amazing.
05:29The fish was me, Tyrus.
05:36Number 16, Oakland Nights, featuring Sia.
05:38No thanks, we don't date ball players.
05:41What, you think we're not sophisticated?
05:42We don't think it, we know it.
05:45If you're a longtime Lonely Island or Oakland Athletics fan, or both,
05:49and you haven't seen the unauthorized Bash Brothers experience, get on it.
05:53If you know nothing about baseball, then you'll probably be pretty lost,
05:56but at least you'll have a good time.
06:11Paying tribute to the legendary careers of Jose Canseco and Mark McGuire,
06:15played by Sandberg and Schaffer respectively,
06:17the two meatheads attempt to pick up two professional gals
06:20played by Jenny Slate and Hannah Simone.
06:22While their awkward attempts at romance may be dead in the water,
06:25we can at least be thankful for Sterling K. Brown's all-in performance as Sia.
06:46In an apparent parody of Macklemore's well-intentioned Same Love,
06:50Connor Forreal attempts to extend a hand to the LGBTQ plus community.
06:54However, gay marriage is now legal,
06:56so it's not entirely clear as to why
06:59Connor thinks this is a problem that still needs to be addressed.
07:10Connor's profound professional loss is our comedy gain.
07:14His efforts to be inclusive are quickly overshadowed
07:16by his obvious fear of appearing to be gay himself.
07:19Note to aspiring pop stars, avoid songs like this.
07:24And also having your music play automatically on washing machines.
07:27Sometimes Connor just gets an idea and he runs with it, you know?
07:30And he's right, like 99.9% of the time, so...
07:51A lovingly gross homage to Slim Thug's song of the same name,
07:54The Lonely Island takes the phrase like a boss in an entirely new direction.
07:59A corporate drone played by Seth Rogen
08:01sits down for an annual review with a boss at an unspecified corporation
08:05and almost immediately gets way more than he bargained for.
08:08Andy Samberg's boss begins by describing what sounds like a fairly routine office job
08:14and quickly goes off the rails.
08:16Call a sex line, cry deeply, demand a refund, eat a bagel!
08:22To give you an idea, his average day ends with an aerial assault on Russia
08:27before flying into the sun and dying.
08:29We hope Samberg's department isn't taking applications.
08:32So that's an average day for you then?
08:34No doubt.
08:35You chop your balls off and die.
08:38Hell yeah.
08:46We love the first Shyroni as much as the next YouTube listicle giant,
08:50but its sequel ratchets up the ridiculousness to a whole new level.
08:54For some reason that even she admits she can't understand,
08:57Rihanna's Clyde recruits Andy Samberg's Shyroni to pull off an old-school bank heist.
09:02Of course, things don't go even remotely as planned thanks to Shyroni's...
09:06well, shyness.
09:08While it ultimately works out for Clyde, who brings home Jon Hamm as a new beau,
09:12we're left wondering if Ronnie makes it out alive.
09:15If his shockingly adept rap skills are to be expected,
09:18we're left wondering if Shyroni is a real-life version of the original.
09:22If not, then who?
09:23If not, then who?
09:24If not, then who?
09:25If not, then who?
09:27If not, then who?
09:28If not, then who?
09:29If not, then who?
09:30If not, then who?
09:32If not, then who?
09:33If not, then who?
09:34If not, then who?
09:36If his shockingly adept rap skills don't keep him out of prison,
09:39we're not sure what will.
09:58You have to hand it to them.
09:59The Lonely Island knows how to not only put together a genuinely great pop song,
10:03but also how to act as a magnet for incredible talent.
10:06In this case, that would be recurring guest Justin Timberlake,
10:10who reprises his role as...
10:12What are these guys' names again?
10:24Anyway, that's secondary.
10:25Gaga manages to steal the show from Sandberg and Timberlake's hopeless,
10:29clueless loverboys while doing her best 80s Madonna impression.
10:33You'll need to watch this one through, oh, we don't know,
10:40maybe a hundred or so times in order to catch all of its perfectly period-accurate references.
10:50With a hook that catchy, we don't think you'll mind.
10:53The two jacktrippers and a Chrissy at the No-Freeze Company.
11:02You guys are still here.
11:15Don't worry, this definitely isn't the last time you'll be seeing
11:18these legendary perverts on our list.
11:20For now, though, this song is another notch in the Lonely Island's comedic belt.
11:24That is to say, Mother Lover is perhaps the raunchiest SNL sketch that's ever made it to air,
11:29but it also works by itself as a legitimately catchy song.
11:41Released from prison following a stint for, what else, indecent exposure,
11:45Sandberg and Timberlake realize that Mother's Day is afoot,
11:48and they haven't done anything to commemorate the holiday.
11:50Fortunately for them, and for us, they think of something.
11:53We can't repeat any of that something, so we think we'll just let them do the talking.
12:18A boombox can change the world, but it can also make for a cringe factor
12:25far beyond what's expected in a typical dance song.
12:28The Lonely Island often starts with a concept not uncommon in whichever genre they're emulating,
12:33and take it to ridiculous extremes that are sure to produce
12:36chuckles, belly laughs, and oftentimes discomfort,
12:39as exemplified in this song's final verse.
12:48We've all heard songs about dancing, letting loose, and throwing social norms to the wind,
13:00but do we still stand by those sentiments when it involves old people and debauchery?
13:05Perhaps not.
13:06Either way, boombox is a hallmark example of the Lonely Island's tendency
13:10for taking things to ridiculous extremes.
13:18The talent behind Lonely Island has managed to infiltrate the music industry,
13:45television, and of course the silver screen,
13:47with pop star Never Stop Never Stopping serving as a shining example of the latter.
13:52Andy Samberg's larger-than-life pop star persona
13:54managed to make fun of many aspects of the entertainment industry,
13:58but Finest Girl takes the cake for its uncomfortable and unnecessary
14:02sexual euphemisms surrounding the killing of Osama Bin Laden.
14:05A handful of friendly faces from the SNL cast made this performance even more enjoyable,
14:19as the pop star draws a parallel between getting down and dirty
14:23and the execution of one of the 21st century's most notorious terrorists.
14:36Oh, to be a fly on the wall when this idea was first pitched.
14:52Instead of slowly devolving into ridiculousness,
14:55this song decided to start there,
14:57and eventually peppered in a taser to the butthole for good measure.
15:01The little things like Samberg's meticulously crafted goatee
15:04underscore the big things, like ruining a child's birthday party.
15:17Of course, the icing on the cake comes from the epic cameos of Elijah Wood and Ryan Reynolds.
15:22Seeing Jake Peralta get beaten down by Deadpool and Frodo Baggins is quite simply magic.
15:31I was screaming and squirming, my butthole was on fire.
15:41With Andy Samberg's larger-than-life comedic personality,
15:45it's sometimes easy to forget that the Lonely Island is a trio,
15:48and Yorma and Akiva are equally hilarious in front of the camera.
15:51Their two-guys act is a great reminder of this,
15:54and also a less-than-subtle jab at those kids in high school
15:57who tried a little too hard to be part of the jock squad.
16:01Everyone is here, I got my snacks, my friends, and a beer.
16:05Just two normal guys hanging out, having fun, right, guy number two?
16:08Yeah, guy number one.
16:10T-shirts just a little too big, an extreme hatred of cheating,
16:13and some unnecessarily crude language towards Steve.
16:16We Like Sports succeeds by lampooning an unexploited niche of social awkwardness.
16:21And we're off to the races.
16:22Then scare the other team with our mad dog faces like...
16:25What, what, what, what, what, what, what, what, what, what, what, what, what.
16:32Whoa, free boat ride for three.
16:36Now, who should I take?
16:39In terms of pure musical talent,
16:41this may very well be their most captivating song.
16:44The jokes are few and far between for a Lonely Island song,
16:47but the flow is oh so catchy.
16:51I'm on a boat, everybody look at me,
16:53cause I'm sailing on a boat.
16:55It's made appearances in clubs, house parties, and spring breaks galore,
17:00each time ensuring that the roof is brought down by the song's end.
17:03T-Pain's remarkable guest performance adds to its enjoyment,
17:06and the chorus is easy to shout along with,
17:09even for those among us who aren't several drinks in.
17:11I'm on a boat, and it's going fast, and
17:14I got an article theme, pass me the afghan.
17:18We feel a little bad that Yorm wasn't invited along for the ride.
17:21It certainly was a memorable one.
17:29Number 5, Lazy Sunday featuring Chris Parnell.
17:32Lazy Sunday, wake up in the late afternoon,
17:35call Parnell just to see how he's doing.
17:37Hello, what up, Paul?
17:39Yo, Sandberg, what's cracking?
17:40In a time when overnight YouTube sensations were not yet a common thing,
17:44the Lonely Island changed the game with their second digital short,
17:47Lazy Sunday.
17:48The unknown group had their big break on Saturday Night Live,
17:51and a two-minute song about nothing solidified their popularity for years to come.
18:01We've all had Lazy Sunday afternoons.
18:04Most of us have snuck food into theaters,
18:06and some of us may have even crushed pre-movie trivia.
18:09The trio proved that larger-than-life tales are not needed for musical success.
18:13Just a dope hook and some sweet nothings that we've all experienced.
18:17The rest is history.
18:31Number 4, Jack Sparrow featuring Michael Bolton.
18:40You might think that you're a cinephile,
18:42but you've got nothing on Michael Bolton.
18:45The Lonely Island set out to make an archetypal song about scoring chicks at the club,
18:49but Bolton was too enamored with the Pirates of the Caribbean saga
18:52to contribute another cliche party hit.
19:06Juxtaposing their efforts with his oblivious dedication to classic adventure movies
19:10is a unique concept that allows for hilarious misunderstandings.
19:14They never quite reach an agreement on artistic intent,
19:17and once again, Lonely Island reigns supreme within the areas of the hilariously inexplicable.
19:35Number 3, I Just Had Sex featuring Akon.
19:44Have you ever felt the urge to tell the world about getting lucky just minutes after it's happened?
19:49The Lonely Island and special guest Akon most certainly have,
19:52and this ludicrous masterpiece does just that in ridiculous fashion.
19:56Best friends? Strangers? Even parents?
19:58Why not let them all know about your sexual exploits?
20:05Nothing and nobody is more important than the fact that you're in a relationship.
20:09Nothing and nobody is off-limits in this free-spirited expression of success in the bedroom.
20:18It's hard not to share in their joyful celebration, as thousands of New Yorkers do just that.
20:23And we're left wondering why bother keep any aspect of our personal life secret
20:27when they're having so much fun doing just the opposite.
20:39Number 2, Jizz in My Pants.
20:54It should come as no shock that the trio's nature could be described as sophomoric.
20:59Does any song exemplify this fact better than this one?
21:03We highly doubt it.
21:04Just the many expressions of bewilderment when the unthinkable happens
21:07make this song side-splittingly funny.
21:17The serious nature and the no-smiles-here mentality make it even better.
21:21Is it relatable or so out there it's hard to do anything other than laugh?
21:33We would prefer not to speculate,
21:34but years later it is still one of their most hilarious and oddly catchy songs.
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22:07Number 1, F**k in a Box featuring Justin Timberlake.
22:18Andy Samberg is joined by Justin Timberlake to make fun of schmoozy love songs by,
22:22well, performers like Justin Timberlake.
22:24The duo is unapologetic and completely oblivious to anything resembling a social norm,
22:30and they proceed to give romantic advice that
22:32unsurprisingly gets them into quite a bit of trouble.
22:46While their misdirected efforts at a thoughtful Mother's Day present are comparably hilarious,
22:50this might be the Lonely Island's best work yet.
23:00When it comes to catchy music with famous celebrities that
23:03leave you in stitches due to its hilarity, the Lonely Island reigns supreme.
23:12What's your favorite Lonely Island song? Let us know in the comments.
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