‘Motherlover’ Made Mother’s Day a Hilarious Boots-Knocking Holiday

What’s endlessly frustrating about Saturday Night Live is that whenever the show hits upon a funny sketch or character, you can bet the writers will quickly run that idea into the ground, bringing it back again and again until you forgot what made it funny in the first place. (David S. Pumpkins, I once loved you, but I don’t need to see you ever again.) 

Click right here to get the best of Cracked sent to your inbox.

So it was understandable to be worried when Justin Timberlake hosted SNL on May 9, 2009. “Oh no,” you probably thought, “they’re not going to do another ‘Dick in a Box,’ are they?” Sure enough they did, but something extraordinary happened: The follow-up was actually pretty fantastic. As we prepare for another Mother’s Day, let us pay tribute to “Motherlover,” the funniest song ever about having sex with your best friend’s mom.

“Dick in a Box” had been the brainchild of Timberlake, Andy Samberg and Samberg’s cohorts in the Lonely Island, Akiva Schaffer and Jorma Taccone, who together created a spot-on parody of the New Jack Swing loverman groups of the early 1990s. Both the song and the video perfectly captured that genre’s aesthetic: Sure, you could enjoy the track on its own, but the visuals of Timberlake and Samberg with their ridiculous facial hair, cheesy dance moves and period-awful clothes really put the concept over-the-top. (And the concept was pretty terrific on its own, anyway.) “Dick in a Box” had aired right before Christmas in 2006 — remember, the “gift” the singers were giving their ladies was for the holidays — and had become an instant sensation. So the temptation was obviously there to revisit the joke for a new song — a temptation Samberg wanted to resist.

“For us, we’re comedians, so our immediate reaction was to be like, ‘No, no way!’ Be scared of trying it again,” Samberg later said of the Lonely Island’s mindset. “And (Timberlake) was like — to his credit — he was like, ‘But what if we did do it again? How unprecedented would that be?’ That’s a big swing. We knew going in from the very start that we were taking a real, real big swing and that if it didn’t work — and if the joke didn’t really land — that we were going to look like big jerks. But you know, he’s so confident and we started writing it and it was making us laugh really hard, so we just went with it, and said, ‘Fuck it.’”

The “Motherlover” beat had been a leftover from the Lonely Island’s first record, Incredibad, which had come out a few months before Timberlake’s SNL hosting gig. “We started singing along to it,” Schaffer said. “Someone mentioned Mother’s Day, then there was a joke about that R. Kelly/Usher song, and we were like, ‘It could be the same girl,’ but then we realized it should be each other’s moms!”

The song he’s referring to is “Same Girl,” a 2007 single in which Kelly and Usher discover that the woman they love is actually the same person. (Sample lyrics: “Man, I can’t believe that / We’ve been messing with / The same girl, the same girl / Thought she was someone I could trust / But she’s been doubling up with us.”) That single’s premise would actually end up better fitting the next song that Lonely Island and Timberlake would do — we’ll get to that a bit later — but, nonetheless, they came up with a storyline in which Timberlake and Samberg’s characters get out of prison after what happened at the end of the “Dick in a Box” video, realizing that Mother’s Day is just around the corner. (In real life, Mother’s Day was the day after that SNL episode.)

Wondering what to buy for Mother’s Day, these pseudo-sensitive singers recognize that their moms are lonely. (The Timberlake character’s mom was abandoned by his father, while Samberg’s character’s father died.) Being compassionate sons who are total morons, they immediately decide that there’s only one course of action: They should have sex with each other’s moms to make them feel better. After all, as they sing in “Motherlover,” “I’m callin’ on you ‘cause I can’t do it myself” — I mean, c’mon, it would be ridiculous if they had sex with their own mom.

Where “Dick in a Box” encapsulated a bygone era of slow-jam music, “Motherlover” wasn’t necessarily tied to a certain genre. (If anything, with its cascading keyboards and high-gloss mixture of pop and hip-hop, the song was mostly a jokier version of the blockbuster smashes Timberlake delivered on 2006’s FutureSex/LoveSounds.) But like the earlier song, “Motherlover” was a dynamite comedy premise, especially because the two guys are so sincere about how much they want to brighten their moms’ mood — and how confident they are that their moms will love this completely inappropriate gesture. (One of the song’s most underrated genius lines is when Timberlake declares at the end, “This is the second best idea that we’ve ever had,” a nod to “Dick in a Box’s” unparalleled greatness/stupidity.) These singers are so dumb but, god bless ‘em, I guess their heart is in the right place?

The recording of the song and the shooting of the Digital Short all happened in the span of a few days, which gave the Lonely Island little time to find someone to play the moms. “We needed a blonde actress who looked like Justin,” Schaffer said, “and I don’t know if I even told the other guys, but I was in a hotel room a week ago, and I turned on the TV and saw the movie No Reservations, and Patricia Clarkson plays the restaurant owner in that. So, I brought her up, and they all said yes immediately.”

As for Susan Sarandon, Timberlake was already friends with the Oscar-winning actress, who talked it over with someone close to her. “I went to my son, who was 15 at the time,” Sarandon recalled, “and I said, ‘They want me (to) do this sequel,’ and he said, ‘Dick in a Box’ is a classic, you have to do it!’”

The video added another joke to the song, which is that although this is objectively a terrible idea for a Mother’s Day present, the two moms actually seem really happy with it. Indeed, the Digital Short is hilarious, in part, because of how much Clarkson and Sarandon invest in their roles as the sexually-satisfied moms. It’s some of the funniest work either of them have ever done — they never wink to the audience or act like they’re above the joke. 

“I think the thing we’ve been finding continually working (at SNL) and reaching (out) to people is that there are so many people out there who are way sillier than you think,” Samberg said at the time, later adding, “(Actors are) really doing dramatic stuff, but they’re not really asked — or given the opportunity — to loosen up and do weirder, sillier stuff. And a lot of them are really excited to do it.”

Schaffer had little time to complete the “Motherlover” clip before the SNL episode. (“We finished the final edits when the show was already on,” he admitted.) But whether or not it’s the equal of “Dick in a Box” — I’m married to someone who thinks it’s even funnier — “Motherlover” felt like a worthy companion piece, proving to be another earworm while actually developing these two characters so that we knew more about them and how stupid they are. 

“‘Dick in a Box’ (is) something that is — and even we can admit it, at this point — well liked by a lot of people,” Samberg said shortly after “Motherlover” debuted. “That’s something that we get a lot of credit and positive energy for, and we didn’t want to ruin it and, you know, like, crap on it by driving it into the mud. But I think it just made us focus really hard and make sure it was something we really believed in.”

Years later, it’s now fairly common that, as Mother’s Day approaches, folks on social media will start invoking “Motherlover.” I can’t imagine ever playing the song for my mom, but there’s this sneakily bighearted message embedded in the track that I think gives it this unexpected wholesomeness. Deep down, “Motherlover” is about appreciating what your mom does for you and demonstrating how much she means. (This, by the way, is in hilarious contrast to another Lonely Island track, “Mama,” which is a send-up of the uber-sincere ballads that rap artists dedicate to their moms — except the trio keep getting mad at their mom for interrupting the recording session.) Plus, “Motherlover” has this really funny homoerotic/incest undercurrent to it as well, suggesting that these guys are so close that they’re totally okay with their buddy fucking their mom. (Another incredible line, from Samberg to Timberlake: “And while you’re in my mother / Make me another brother / And while I’m in your mother / I’ll never use a rubber.”)

To date, the Lonely Island and Timberlake have only collaborated one more time, on the 2011 song/video “3-Way (The Golden Rule).” It was a more direct nod to the lyrics of “Same Girl,” with Timberlake and Samberg each about to meet their special lady, then realizing they’re both dating Lady Gaga and deciding, what the hell, they’ll have a threesome. (“It’s okay / When it’s in a 3-way / It’s not gay / When it’s in a 3-way / With a honey in the middle / There’s some leeway.”) 

It’s pretty funny too, although it doesn’t live up to the one-two combo of “Dick in a Box” and “Motherlover” — however, it’s not such a letdown that it makes you retroactively hate their earlier songs. When you consider how often SNL jumps the shark with their best sketches through overexposure, the Timberlake/Lonely Island three-peat achievement is even more impressive. I hope they never work on another song together. But I’m so glad Samberg decided to take Timberlake up on his challenge to take a big swing with “Motherlover.” It would be my honor to be their new stepfather.