The following blog post is a companion piece to the newest episode of the We Heart Hader Podcast. Give us a listen, won't you?
Santa's My Boyfriend
Amy Poehler, Maya Rudolph and Kristen Wiig take a break from trimming their Christmas tree to sing of their extramarital affair with jolly ol’ St. Nick himself
- This is one of two segments from this episode that will be no doubt familiar to those who tune into the same ol’ primetime SNL Christmas special every year or are just fans of 2000s era SNLs’ female cast in general.
- The ladies actually sing well and can carry a tune. This sketch makes good use of their genuine singing talents, especially Maya who actually can sing well in her own voice when she's not mocking another female singer's vocal style or just purposely singing badly for comedic effect.
- Real crowd pleasing stuff here with the ladies singing vaguely suggestive but very primetime friendly PG lyrics representing what their idea of an affair with Santa Claus would be like. I guess with this week's host and this being the Christmas show the girls must've either known or heard Lornes’ casual warning to Samberg and his boys that “kids will be watching”.
- I did get a slight kick out of the line about Santa “leaving his bitch of a wife” for them. I wasn't quite as crazy about their self deluded naivete about breaking up a marriage being written in there.
- The ending with the girls singing LFNY to the tune of “Oh Holy Night” was lovely and possibly my favorite part of this. B-
Monologue
Justin Timberlake sings “The Chipmunk Song” with world famous chipmunks Simon (Armisen), Theodore (Samberg) and a too-cool, disinterested Alvin (Hader)
- This sure as hell beats a glorified segue into Justin singing another one of his own songs or just a song crafted by SNLs’ writers that's just a rough approximation of his style of modern mainstream pop music but…y'know ABOUT his experience navigating through a typical SNL episode.
- This is definitely the type of thing that sounds a lot cornier on paper but the guys really bought an extra goofy cartoon charm to it in execution that was unexpected.
- Considering Bill, Fred and Andy are playing cartoon animal characters brought to life, I appreciate that the makeup didn't extend beyond “teeth”. Like, from a purely visual standpoint, I appreciate that the guys were essentially playing human versions of the chipmunks (or maybe the lack of makeup is this season's budget cuts on display once again?)
- Armisen didn't seem to add much beyond background vocals and Timberlake is no Dave Saville but I got a kick out of Sambergs’ giggle as Theodore and Hader’s whole non-singing performance, flirting with a woman in the audience. His “dude…seriously” lines had shades of his Frankenstein character from Hugh Lauries’ episode.
- Most of all, I'm glad this characterization of the chipmunks is based more on the 60s’ records and 80s’ cartoon than the slightly douchey late 00s live action CGI movies that weren't even out yet at this time.
- I couldn't help but notice that Bill had his left hand in Justin's right arm near the end. I wonder if this was an anxiety thing? It didn't look like it on the surface and it's not one I've heard about in the course of my research for this podcast so he may not have talked about it in interviews to my knowledge. B-
Competing Charities
A humble Salvation Army Santa (Forte) puts up with a big flashy mascot for a charity shelter simply known as “Homelessville” (Timberlake) encroaching on his turf. Dressed as a giant Cup O’ Soup, he sings and dances to hip hop tunes from his boom box. They almost come to physical blows but then realize the good they could do by working together.
- I've tended to run pretty hot & cold on these “dancing mascot” sketches. I liked these earlier ones just fine and as long as the song parodies are done well and audible, I'm mostly OK with them.
- I thought Parnell, Forte and (at one time later) Moynihan were the best foils to Timberlakes’ character so those were among the ones I liked, but some of the later ones felt a little overlong, a lot more self indulgent and more than a little overdone.
- To put it another way, these sketches were pretty much the same thing to Justin Timberlakes’ episodes as the NYC Broadway Musical Medley sketches were to John Mulaney's episodes when he became a regular host.
- As for this one in particular, it mostly had everything going for it. The songs were quick and to the point. They were all upbeat 90s hip hop jams meant to keep up the energy and keep the sketch moving along (well, except for Snoop Doggs’ “Drop It Like It's Hot” which I still got a kick out of along with the “Tootsie Roll/Minestrone” parody).
- I do like how Timberlake's songs in this one were purposely not too long or self indulgent since this was one of the episodes where he was pulling double duty so he was fully aware he was going to actually get to sing and dance for real and didn't need to take his sweet time in these sketches to fulfill his need to perform musically or make love to the camera or just generally stroke his ego too hard here.
- Fortes’ eerie falsetto played well against Timberlakes’ pop star energy. I especially like Wills’ line questioning whether “there's even a legitimate charity called ‘Homelessville'”.
- The ending was charming. I liked the ones where they end up both working together instead of one person just bailing on the whole sketch so Justin can sing and dance some more or they just let the sketch fall apart.
- Other than that, the only thing that dragged this sketch down was the toothless PG-13 Disney Channel/Nickelodeon feel Timberlake's part had which even seeped through in his line about how “Christmas isn't supposed to be about Santa kicking a cup of soup in the croutons”. I know, I know, it's Christmas, it's the mid 2000s and kids may be watching, but still… B-
Target Lady
The Target Lady (Wiig) and stock boy Marcus (Timberlake) irritate and drive away customers (Rudolph & Forte). The Target Lady rambles about irrelevant details and runs off to grab similar merchandise to what customers have on them as they come in. Marcus prattles on about how the Chapstick he is applying to his chapped and burnt lips is giving him an allergic reaction.
- Well, I remember these sketches mostly from being done mostly before Kristen Wiig moved on to even more hammy, self indulgent and obnoxious characters, so…these are another thing from this era I never had too much of a problem with…compared to later Kristen Wiig characters. Still, there didn't seem to be a lot here.
- Timberlake's character was harmless and dull here. I did like the makeup job they did on his lips though. They would do one of these in the next episode he would host where he was in goofy old lady drag playing the character of “classic Peg” that really annoyed the hell out of me.
- These sketches are all very dialogue heavy and tend to follow the same formula so I can't really pick out any particular stand out moments (I didn't really have any here to be honest). C+
Digital Short: Dick In A Box
Two smooth talking early 90s style R&B singers (Timberlake & Samberg) sing about presenting their gift wrapped genitalia to their women (Rudolph & Wiig) as a “special” holiday gift…for every possible occasion.
- Well, what ELSE can be said about this overplayed classic that hasn't already been said?
- I personally would classify this in the same category as “Lazy Sunday” in that it was one of those sketches that I didn't know at the time it aired that I was seeing a future classic in the making.
- Certainly, I was aware I was seeing a standout moment that felt much more brash and drastically different from everything else the show was doing at the time but it wasn't until I saw how this sketch blew up online shortly after the fact that I saw this become an era defining moment of the show that signaled a drastic shift in style and tone was coming (or in this case had fully arrived).
- The audience must have felt this exact same way too seeing as this got quite a bit of screaming laughter and they even broke into sudden applause during one of the parts you could obviously tell was taped in Conans’ studio at the time.
- Sure, a large part of the appeal to this may be due to it playing to a live audience full of younger fans of the hottest male pop star of the moment singing about his penis, but this had a bit more going for it than that.
- Obviously, this is the other piece from this episode that gets played a lot in modern prime time Christmas compilations. In fact, I think they're just straight up bookends by this and “Santa's My Boyfriend” at this point.
- As overplayed as this may have been in subsequent years, you'd be hard pressed to find any SNL fan who didn't like this (or just openly said they hated it) at the time.
- Anyway, as someone who has always liked Andy Samberg and The Lonely Island on the show in general and is of the right age to see how hugely influential they were to millennial comedy in general, I liked this then and still like it now.
- Part of the reason this works so well aside from Timberlake is that it's a tightly edited pretape and essentially a music video done in an era when SNL wasn't doing them (probably since they were more MADtvs thing at this point anyway).
- Another part is the sheer commitment to such a silly dumb joke (especially from Maya and Kristen) seeing as the idea for this stemmed from both Samberg and Timberlake bonding that week over their shared love of early ‘90s Color Me Badd style R&B they grew up on, so it's another genre spoof done with love and affection for its subject.
- Timberlake just being in his element helped this a lot, too. He contrasted well against Andy trying to put his part over on sheer charisma.
- A couple of his moments that got me were his intense stares into the camera while wearing the various costumes for each holiday Samberg mentioned as well as the final shot of them getting handcuffed and shoved into a police car. See, The Lonely Island DOES have a social conscience! B+
Barry Gibb Talk Show
Barry (Jimmy Fallon) and Robin (Timberlake) Gibb alternately interview and berate Sandra Day O'Connor (Wiig) NY Times Columnist Thomas Friedman (Armisen) and former US President Jimmy Carter (Hammond)
- This is another series of Timberlake staple sketches I have always run hot and cold on. I liked the first two the most and this third in the series was okay, but I really didn't think they needed to be done anymore after that.
- Still, I totally understand why a performer like Justin Timberlake would feel the need to do this every time he is either the host or musical guest whenever Jimmy Fallon is in the building seeing as he started his career in the world of pop music where you're just expected to play the old hits on stage each night because that's what the crowd came to hear from you.
- I can see why he would apply that approach to comedy as well since he hasn't had much acting experience under his belt at this time and he never came from a background of writing or improvising comedy either.
- Speaking of Jimmy Fallon, I'd imagine it must've been nice to see him come back for a cameo on SNL since at this point, he'd only made a couple of quickly forgotten movies since being away from the show and he was still a few years away from taking Conans’ old slot for the first time.
- Anyway, I liked how this sketch didn't feel as unnecessarily stretched out as future editions of The Barry Gibb Talk Show did while still giving Fallons’ Barry Gibb character enough breathing room to let two of his guests actually get a word in edgewise to him and respond to his question before he just starts threatening them.
- Speaking of, back in the fifth episode of the podcast, my cohost Deej mentioned that one of Lorne's criticisms of Bills’ first Vincent Price sketch was “why would guests keep coming back on his show if he's going to be mean to them?” and Bill took that to heart changing his role to the put upon host dealing with his guests craziness. Clearly, Lorne should've brought this up to Jimmy, Justin and Steve Higgins in between the first two Barry Gibb Talk Show sketches. C+
Dry Eyes
A game show where host Gary Pierce (Hader) challenges contestants NOT to cry at heartbreaking/heartwarming scenarios and quotes researched from their own real personal lives or during a medley of emotionally charged songs during the final speed round. Today's competitors are school teacher Jerry Bertrand (Armisen) and 22 time returning champion firefighter Brett O'Connor (Timberlake)
- Hey, it's Bills’ FIRST game show host role that Deej & I somehow failed or just flat out forgot to include in our episode dedicated solely to Bill's game show host roles! Good for him for getting to break out in such a “utility man” capacity in such a notable episode! He was solid in a snarky support role here. Shades of Vince Blight?
- Anyway, I actually quite liked this sketch. Armisen and Timberlake were great in it. I liked Fred's drastic tonal shift to immediately crying and being dragged away by Wiig with the Kleenex consolation gift basket “for losers”.
- I especially liked Justin's wide eyed facial expressions he made to steel himself from crying (especially during the medley of Aerosmiths’ “Cryin'” Lionel Richies’ “Hello”, Celine Dion's “My Heart Will Go On” and Harry Chapins’ “Cats’ In The Cradle”).
- I loved his casually blowing off the major self induced heartbreak and family neglect in his life just to win on a game show (to the point where he tells his own father to “suck it for eternity” for leaving when he was 13).
- One thing that makes this sketch work so well is it being a product of its era. It's so specifically crafted to this season and these performers that I can't really imagine any other hosts or cast members performing these parts. Ok, maybe I could see them trying this with Ashton Kutcher around this time, but he would drag it down somehow, I'm sure.
- I don't know if “toxic masculinity” was even being discussed in 2006 but today, this sketch could be seen as great subtle satire on it (especially with Bills’ barely audible line at the end that sounded like “better get to know a therapist?”) B-
Justin Timberlake Performs “My Love” & “What Goes Around”
- It's worth noting that Justin's first performance was introduced by Cameron Diaz (which I guess makes sense because they may have still been dating at this time so he could still call her “my love”) and his second performance was introduced by Jimmy Fallon…in a Beatles accent…because he was in the building?
- Oh, this second song is one of the songs about him and Britney cheating on each other. Yeah, that'll be a real good look for ya there, bud. Hell, it might be an even better look for the show considering what follows it.
- Yeah, I don't really have much to say about either of these songs other than they're pretty much exactly what you would expect from Justin Timberlake in this time period.
Weekend Update w/Poehler & Meyers
Lou Dobbs (Hammond) delivers a commentary on immigration reform and proposes several insane solutions.
The Gay Couple From New Jersey (Armisen & Hader) comment on their state's continued recognition of civil unions.
- Joke-wise, all that stood out to me so far were “Bush/nativity scene”, “tiny loans/stripping” and “Rumsfeld/Bin Laden”.
- I only vaguely remember who Lou Dobbs was so I can't really judge the accuracy of Darrell's impression. It sounds like a more toned down version of his Ted Koppel but since it's Darrell Hammond I'll trust that he got the voice right.
- I will say I'm glad they found a way to do a commentary on immigration of all subjects that doesn't sound too prescient as to apply to today's political situation and that I liked Darrell's cable news deadpan juxtaposed with lines about how we should build two 700 mile long walls (the second one having a sign that says “Wall 2 Of 50”) and a 700 mile long trap door with a just as long slide made me laugh. Speaking of, this is one of two strange cable news themed pieces that barely had any business being in THIS episode at all, but we'll get to the other one later.
- Ok, I liked Seth's “world's oldest person”, “Obama/Bush/did we catch ‘im?” and “Amish Blackberry” jokes. I even liked the joke about the fence company in California who hired undocumented immigrants to build a fence between California and Mexico.
- Still not too crazy about the return of the gay couple from NJ, but I did like Bills’ meat freezer joke along with the one about NJ not being as “gay” as Connecticut or Vermont (the only other two states to allow same sex civil unions around this time…which, yeah, that definitely wouldn't fly today but I'll let it slide given how it fits both the characters AND the time period). The mistletoe gag was a nice touch and a decent button to end this on. C+
Hip Hop Kids
After finding themselves trapped in a mineshaft for hours on end, Trey-J (Timberlake), Girlie-T (Poehler) and silent DJ K-Smoove (Thompson) start to question whether their go-to solution of dancing through their problems actually helped or hurt them. So far, all their break dancing has only gotten their friends Keisha (Wiig) and Jo-Jessica (Rudolph) killed by falling rocks and their other friend Flip Flop (Sudeikis) eaten by cave creatures (Hader & Forte) their dancing has attracted…which gave them the idea to eat Keisha and Jo-Jessica to stay alive only to find that they couldn't dance their way through a tiny crack of light.
- Hmm…this sketch seemed like it was constantly fighting against itself but there was just enough self aware stupidity in this to balance out what may have been too obnoxious to work. At least I can't say at any point that this felt too much like an All That sketch.
- Much like Justin's first musical performance, this kind of leans too heavily into the worst aspects of his whole “image” around this time.
- I liked the stalactite/stalagmite argument between Amy & Maya and Sudeikis was great with the few lines he had (even up to getting eaten by cave creatures).
- Other than that, not a whole lot else stood out to me but at no point was I actively rooting against this sketch. C+
Elf Audition
Shelby Hastings (Timberlake) auditions to be a Macy's Elf with the help of her mother Virginica (Thompson). Two beleaguered agents (Armisen & Hader) only reluctantly give Shelby the part to get Virginica to stop seducing them.
- Uuugghhh…another one of these sketches.
- At least Justin only ever did one more sketch like this on SNL that I can remember. Thank God Kenan swore off drag roles like these…eventually…after six more years.
- I got a mild kick out of Kristen's part at the beginning and Justin's heavily bejeweled glittery cellphone with a wacky sound effect ring tone. Other than that, I don't really WANT to say anything about this sketch. D-
A Holiday Message From Nancy Grace
Nancy Grace (Poehler) calls for more compassion for the exotic dancers who was just found to have falsely accused three Duke University LaCrosse players of sexual assault and threatens to hunt down those Duke LaCrosse players, pull out and eat their still beating hearts.
- Jesus Christ, what the fuck WAS this thing? Why was this allowed to air at the end of a Christmas show with a big pop star host? Who the hell was this for?
- I mean, my main takeaway from this is that the writers (probably Jim Downey if I had to guess) really wanted to make Nancy Grace look like an ass for very publicly supporting someone who made a false accusation of sexual assault?
- Yeah, this is WAY too dicey of a topic to really get into whether they had the right take or not. I'll just say it would've played differently today and they probably wouldn't handle this at all if there were no other way to handle it (which is obvious).
- I did actually laugh at her threats to rip out and eat the still beating hearts of the Duke LaCrosse players. Maybe the sheer chaos and insanity of this piece just looped back around to the point where part of it was funny? C-
Band Shot
- Ok, something was obviously cut for time here and it could've only been one of two things. Here's my theories as to what may have gotten cut...
Michael McDonald's McDonald's
Former Doobie Brothers front man Michael McDonald (Timberlake) advertises his own fast food restaurant. This sketch quickly devolves into McDonald listing off various legal troubles he's been having with the restaurant itself, the least of which include the fact that there is already a fast food restaurant called “McDonald's”. Also, McDonald didn't have the necessary permits to open the restaurant and, as he sings to the tune of “What A Fool Believes”, “the sign fell off the rooooooof and it landed on the top of a school bus”.
- I know I heard Timberlake talk about this sketch on The Daily Show around this time. Also, SNL writer Emily Spivey talked about this sketch on Late Night w/Seth Meyers. They mentioned Colin Jost wrote it and even showed a brief clip which you can see here.
Quitting Time
Justin and Fred are stocking shelves in a big box Walmart type store. Justin is dancing, beatboxing and bragging about how he gets off at 5:00 instead of doing any actual work. Suddenly, Maya comes in as his boss and tells him he needs to stay until 11:00 to cover the shift of a coworker who called in sick…so Justin now brags about getting off at 11:00.
- This was apparently included on the Best of 06/07 DVD. I only saw it because it was uploaded to either Vimeo or Dailymotion or some such “alternative” video site. As of this writing, I haven't been able to find it again…but I have seen it once, and it wasn't that great.
Overall Thoughts
- Well, this episode as a whole is…about as uneven as I expected it would be.
- Hey, this is the second episode in the first half of a season with a male double duty host at their peak of popularity who's there to put the last show before an upcoming holiday break over on his sheer charisma and energy.
- The main difference between JT and Luda here being that the former is relying much more on his crowd pleasing pop star talents, falling back on his ability to sing and dance his way through every other sketch.
- Still, he did a solid job. It's easy to forget that at one time Justin Timberlake was actually a welcome presence on SNL before his time had passed and the general public wasn't that interested in seeing him anymore (as is the way with most pop stars who don't later carve out a specific niche for themselves).
- This is one of those episodes that's mainly remembered for one or two “classic” moments that later get replayed and discussed as being among the show's “greatest hits”.
- Of course this also means that it's one of those episodes where when you look back at this one as a whole, you start to think that the entire episode doesn't quite measure up to its’ “classic” moments and may not have earned the “classic episode” status…outside of those specific moments.
- Still, what worked well really did hit and what didn't hit was mostly just dragged down by lame “pandering” humor since the host is someone they mainly bring out when they want to appeal to as wide an audience as possible (big Christmas show with families watching, big pop star host that the kids like, etc.)
- What's interesting about this episode is that it's only Justin Timberlakes’ second time hosting. We know now that Justin is one of those hosts that relies on certain recurring characters quite a bit, but only one character of his of the whole night was already an established recurring sketch (Robin Gibb…I'm not counting Virginica or Target Lady here since those didn't originate in his previous hosting stint).
- His other well known recurring characters either made their debut tonight (Dick In A Box) or are only being performed for the second time (Dancing Mascot) thus establishing them as “recurring” for the first time ever.
Closing Thoughts
- Well, the next full length episode from this season we do for the podcast and I for this blog might be either Julia Louis-Dreyfus/Snow Patrol or MAYBE Zach Braff/Maroon 5. We haven't fully planned it out yet, but that's all I can tell you at this point.
- Other than that, I don't know what other SNL episodes I might be reviewing for this blog until the new season starts on October 4th.
- I will say though that I will be posting a brand new review of a mystery episode from a completely different era i have never reviewed before on this blog on Tuesday, September 9th, 2025. That day, I will also be reposting two "classic" episode reviews with new thoughts and commentary.
- I really can't tell you which episodes those will be. I mean, as of this publishing I myself DO know which specific episodes those will be, but I can't reveal them at this time and place. I can just say I did NOT pick them myself. They have been picked for me.
- All I can say for sure is that you can all find out which episodes I will be reviewing in real time all together on Tuesday, September 2nd starting at 8PM EST time…when I will be appearing on the Saturday Night Networks’ 50 Greatest Episodes Of All Time Countdown with Jon Schneider, Bill Kenney and others.
- The only other thing I can say for now without spoiling anything is that two of the episodes I will be talking about on the SNN countdown are ones that I have already reviewed on this blog a number of years ago. Still, they're ones that aired just long enough ago to feel like they're from a completely different time, so I felt it necessary to see how well they still hold up in 2025 so that's why I will be reposting my old reviews with fresh, new commentary added.
- I vaguely remember Stooge having done something like this on the old Voy board around 2017-ish but since I can't find an example of that to post here to show you, just think of this like one of those old "rerun plus" episodes of 80s NBC era David Letterman.
- Be there! See you again soon!
