20 funniest roles, raps and moments of Andy Samberg’s career

Andy Samberg and childhood friends Jorma Taccone and Akiva Schaffer (a hip-hip comedy trio collectively known as The Lonely Island) joined “Saturday Night Live” in 2005 with all three as writers and Samberg as a cast member. Unlike most “SNL” staffers, the boys didn’t do a traditional audition and instead were hired based on their homemade viral videos. Shortly after joining, while looking for their first hit, the trio reached into their idea bag and brought to fruition a parody of the famous shooting scene at the end of season two of “The O.C.” Except, in the “SNL” version, everybody involved shoots each other as the “Mmm whatcha say” music plays, including two cops played by Fred Armisen and Jason Sudeikis. The sketch, titled “Dear Sister,” didn’t make Samberg a household name yet, but it certainly put him on the map among fans of “SNL.”

Written in a single night by Samberg, Schaffer, Taccone and “SNL” cast member Chris Parnell, the SNL Digital Short “Lazy Sunday” is a lighthearted yet aggressive rap that spins a yarn about Samberg and Parnell hitting up Manhattan’s Magnolia Bakery for some cupcakes before seeing “The Chronicles of Narnia” at a local theater. The Lonely Island thought the song and music video would be a flop, but Lorne Michaels had faith in it, and in retrospect, “Lazy Sunday” is credited for launching the career of The Lonely Island, revitalizing “SNL” and even helping boost traffic to YouTube during its first year of existence. 

The Lonely Island’s songs would eventually become known for being injected with some serious star power, but that didn’t begin until Justin Timberlake hosted “SNL” on Dec. 16, 2006 and appeared in the song and video for “Dick in a Box.” Written specifically to showcase Timberlake’s vocals, the song became an instant sensation and even earned a win for Outstanding Music and Lyrics at the Creative Arts Emmys. Timberlake would team up with The Lonely Island again in the coming years for “Motherlover” and “3-Way (The Golden Rule),” but neither could match the enormous success of their first collaboration.

After the early success of The Lonely Island on “SNL,” the trio decided to make its first feature film and managed to get the backing of both Lorne Michaels and Will Ferrell as producers. With Akiva Schaffer at the helm, Andy Samberg starred in “Hot Rod” as Rod Kimble, an amateur stuntman who plans a dangerous jump to raise money for his stepfather’s heart surgery. Rod doesn’t particularly care about his insulting and unsupportive stepdad, but he wants to keep the old guy alive long enough to prove himself as a man and finally beat him in a sparring match. Jorma Taccone, Danny McBride, Isla Fisher, Bill Hader and a few other famous faces round out the cast of this 2007 comedy, which was a box office bomb but actually received some solid reviews.

Andy Samberg doesn’t get a lot of credit for his impressions, but he actually performed a few great ones during his six-year stint on “Saturday Night Live,” including a dead-on impersonation of Mark Wahlberg. The two sketches, “Mark Wahlberg Talks to Animals” and “Mark Wahlberg Talks to Christmas Animals,” were painfully simple: They solely consisted of Wahlberg (Samberg) making one-sided small talk with actual animals, with the conversations almost always ending with the line, “Say hi to your mother for me.” The real Wahlberg publicly expressed his displeasure with the sketch, but after receiving some backlash, he made a surprise appearance on the following week’s episode of “SNL” to have a comedic confrontation with Samberg.

It may have been just a supporting role, but we loved Andy Samberg in “I Love You, Man.” In the acclaimed 2009 buddy comedy, he plays Paul Rudd’s character’s gay younger brother, Robbie, who gives Rudd advice on making friends with men and sets him up on a “man date” with the awkward pipsqueak Lonnie (Joe Lo Truglio). The good-natured Robbie is also referred to as one of two best friends of the brothers’ dad (J.K. Simmons)...but hilariously, his first-born son (Rudd) is not the other one.

By 2009, The Lonely Island were so popular that their SNL Digital Shorts didn’t even need to appear during the show’s broadcast to become popular. The music video for “I’m on a Boat” was dropped on Feb. 3, 2009 in anticipation of the group’s upcoming debut album, “Incredibad,” and managed to break into the mainstream music charts in a monumental way, soaring as high as No. 56 on the Billboard Hot 100 and becoming certified platinum. Although the rap tune appears to fit in the genre well, as the video takes place on a yacht and both the song and video feature T-Pain, it actually contains comically mundane and profane lyrics about being on a boat, such as “I'm on the deck with my boys, motherf*cker / This boat engine make noise, motherf*cker.”

Like most of The Lonely Island’s songs, the lyrics to “Like a Boss” gradually transition from mundane to obscene in the group’s traditional aggressive style as Samberg — playing a middle-management businessman — lists all the things he does “like a boss” on a daily basis. This includes everything from sending faxes and promoting synergy to hooking up with a giant fish, crashing into the sun and dying. “Like a Boss” helped round out the “Incredibad” album, but believe it or not, the song is also credited with bringing the phrase “like a boss” into the mainstream, as it wasn’t used especially often before the Lonely Island’s SNL Digital Short aired on April 4, 2009.

Shy Ronnie is a red-headed, bespectacled rap enthusiast who can mumble inaudibly only when paired up with his duet partner, Rihanna, but is actually capable of spitting some loud, profanity-laced lyrics. The duo debuted on “Saturday Night Live” on Dec. 5, 2009 in a sketch that saw them performing in front of a grade-school class and returned for “Shy Ronnie 2: Ronnie and Clyde” in an episode two years later. In the latter sketch, Ronnie and Rihanna were bank robbers, making for an equally entertaining rap performance that also included a cameo from that week’s host, Jon Hamm. Somewhat shockingly, the original skit actually received an Emmy nomination for Outstanding Original Music and Lyrics.

Andy Samberg was already close with Amy Poehler from their mutual time on “SNL,” so it makes sense that the actor would appear on “Parks and Recreation” at some point. Samberg was in only one episode and his part was minor, but he was nevertheless a perfect fit as Carl Lorthner, the head of all outdoor security who is known for always talking in a loud voice. And he talks constantly. Apparently, Carl used to have an indoor desk job but had to transfer to an outside position for obvious reasons.

In the song and video for the SNL Digital Short “Jack Sparrow,” The Lonely Island guys bring in Michael Bolton to contribute to a song about living large. But having just watched a “Pirates of the Caribbean” marathon, Bolton wants to sing only about Johnny Depp’s swashbuckling pirate character. Eventually the iconic singer moves on, only to end up crooning about “Forrest Gump,” “Erin Brockovich” and “Scarface” instead. Despite being hesitant to use some of the song’s harsh language (including an F-bomb), Bolton called the song “one of the highlights of my career and most memorable experiences of my life.” “Jack Sparrow” was generally viewed as the funniest sketch of the May 7, 2011 episode of “SNL,” and the single reached No. 65 on the Billboard Hot 100.

When Andy Samberg debuted his Nicolas Cage impression on “Saturday Night Live” in 2010, it was received well enough. He sort of looked like Cage and did a respectable impersonation, but the Weekend Update segment was still missing something. Samberg reprised the character on Weekend Update two years later, only this time he was accompanied by the actual Nicolas Cage. This sketch was infinitely funnier, as not only was it hilarious to see Fake Nic sitting right next to Real Nic, but the latter also took some shots at Samberg’s interpretation of himself, calling his version “an exaggerated, screaming psychopath.” According to Samberg, after the skit was complete, Cage said it was a pleasure doing business with him, “and then just disappeared into the darkness, and I've never seen him again. I don't know if he was ever really there. It was great.”

Casting Andy Samberg as the lead in a romantic dramedy seemed against the type, but the actor received positive reviews for his role in 2012’s “Celeste and Jesse Forever” opposite Rashida Jones (who also co-wrote the film with Will McCormack). Samberg and Jones play a couple who dated and married young, end up getting divorced and attempt to remain friends while both separately struggle with their lingering feelings for one another. Roger Ebert gave the film 3.5 out of four stars, and “Celeste and Jesse Forever” owns a 70 percent rating on Rotten Tomatoes.

Critics and audiences alike enjoyed Andy Samberg’s stint on “Cuckoo” as Dale Ashbrick, a drug-taking hippie who marries a medical student named Rachel (Tamla Kari), much to the chagrin of her parents (Greg Davies and Helen Baxendale). The always-eccentric Samberg stole the show opposite Davies in the BBC comedy, which was renewed for a second season in 2013. However, due to his increasingly hectic schedule, Samberg left the show after the first series and was replaced by Taylor Lautner, who played the former’s long lost son.

When an ordinary backpacker named Jonathan (Andy Samberg) stumbles upon the Hotel Transylvania, a human-free lodging run by the 532-year-old Count Dracula (Adam Sandler), chaos and hilarity both ensue, especially after Dracula’s daughter Mavis (Selena Gomez) and Jonathan fall for each other. Although Samberg had previously dabbled in voice acting, this was his first major role in a feature film, which was successful enough among kids and adults alike to yield sequels in 2015 (“Hotel Transylvania 2”) and 2018 (“Hotel Transylvania 3: Summer Vacation”).

The cop sitcom “Brooklyn Nine-Nine” is armed with a strong cast that includes Andre Braugher, Melissa Fumero, Stephanie Beatriz, Terry Crews, Joe Lo Truglio and Chelsea Peretti, but Andy Samberg is undoubtedly the centerpiece of the group. His character, detective Jake Peralta, is a laid-back, immature prankster who also happens to hold the highest number of arrests in the precinct, creating ample opportunities for hijinx. Samberg won a Golden Globe in 2014 for his role, in addition to numerous People’s Choice and Teen Choice Award nominations. FOX canceled the series after five seasons of steadily declining ratings, but NBC picked up the fan favorite the next day.

The Isner–Mahut match at the 2010 Wimbledon Championships took 11 hours, five minutes to play over the course of three separate days. This was already a comically long time for a tennis match, so writer/producer Murray Miller re-imagined and exaggerated it as a seven-day-long event for his 2015 HBO mockumentary, “7 Days in Hell.” Andy Samberg played Aaron Williams, the fictional “Bad Boy of Tennis” opposite his opponent and nemesis Charles Poole, played by Kit Harington. The star-studded, absurd mockumentary managed to draw 579,000 viewers when it aired on July 11, 2015 and owns an 80 percent freshness rating on Rotten Tomatoes.

After cutting his teeth as a host of the 2009 MTV Movie Awards, Samberg was given the reins of the 67th Primetime Emmy Awards six years later. Samberg was his silly self throughout the broadcast, for the most part avoiding controversial jokes and shining best in a prerecorded bit at the beginning that involved him watching every previous Emmy event. Although somewhat forgettable, Samberg’s stint as an Emmy host was still solid enough for him to earn a spot in our list of the Top-25 Emmy Hosts of All Time.

Don’t let the paltry box office numbers ($9.6 million against a budget of $20 million) fool you, “Popstar: Never Stop Never Stopping” is actually a very entertaining mockumentary that focuses on the rise of Conner Friel (Andy Samberg), a musical prodigy who dreams of becoming a star. Written by, produced and starring Samberg, Jorma Taccone and Akiva Schaffer (and directed by the latter), “Popstar” also features a veritable who’s-who of comedians in its cast, including but not limited to Sarah Silverman, Tim Meadows, Maya Rudolph, Bill Hader, Will Forte, Will Arnett and “Weird Al” Yankovic, in addition to some three-dozen cameos. Worth seeing simply for the star power alone, “Popstar” also earned an admirable 78 percent freshness rating on Rotten Tomatoes.

Looking to create a suitable successor to “7 Days in Hell,” Andy Samberg and a handful of producers next tackled the sport of cycling — specifically the Tour de France. In Samberg’s exaggerated illustration of the doping scandals that plagued the event, all participating cyclists are suspected of cheating. But instead of canceling the whole race, the Union Cycliste Internationale allows five cyclists — the only ones who didn’t attempt to bribe the UCI president — to continue. This group includes Marty Hass (Samberg), an American-born Nigerian who is resented by his countrymen for being their sole representative. The others are played by Orlando Bloom, John Cena, Freddie Highmore and Daveed Diggs — a zany formula for an outlandish film that worked surprisingly well and earned overwhelmingly positive reviews from critics.