Justin Timberlake’s Lifetime Pass


When it was announced that Justin Timberlake was releasing The 20/20 Experience, his first album in almost a decade, internet commentators exploded into a vigorous fight to give the most begrudgingiest of all begrudging admissions that the dude, sigh, actually has some talent.

Face it, JT is our generation’s Frank Sinatra. He acts, he sings, he does comedy and he is an all around entertainer. Lest anyone think the comparison is sacrilege, remember that in his time some derided Sinatra as both a poor singer and a lousy actor. Plus, his career began as a teenage heartthrob, pretty much the same as Timberlake. The similarities are uncanny.

If I wanted to make the case for JT’s lasting legacy, I wouldn’t have to search far. Even with only two albums released to date, he’s built up an impressive bullpen of classic pop songs, and The 20/20 Experience looks to further his dominance. He’s been in some forgettable films, but he’s also been smart enough to land memorable parts in both critically-acclaimed films and sure-fire cult classics.

Culture critics will be arguing the lows and highs of his career for years, but there are a few moments in his career that rise above the debate. These are the moments that even Timberlake’s most adamant haters will pretty much universally say, “Yeah, that was good.”

With a week until the new album drops, here are the career highlights that give Justin Timberlake a Lifetime Pass:

Dick in a Box

Both “Motherlover” and “3 Way (The Golden Rule)” were surprisingly funny, considering that these sorts of jokes tend to have diminishing returns. That said, the original collaboration with Andy Samberg is still the crown jewel of this threesome of hilarious videos. Watching the original SNL clip (with the audience laughter) is a great reminder of just how unexpected and wonderful the original viewing was for all of us. Nobody dislikes this video (unless they’re dead inside).

History of Rap

Love JT or hate him, rap fan or not, no one can deny the pure entertainment value of him and Jimmy Fallon giving a history lesson on the most popular music form in the world. My favorite part? They acknowledge that “Ice, Ice, Baby” was a thing (to the delight of screaming white sorority girls everywhere) but they don’t actually dignify it by performing any of the lyrics.

My Love

I’m not going to say this is my favorite JT song, but then again, it isn’t not my favorite JT song. Regardless, it is the one song that everyone admits to liking, even if they do it with shame-averted eyes. It’s an undeniable force that so perfectly captures what worked on mid-2000s radio that to hate it is to hate a decade’s worth of pop music. Some people might want to try to maintain that position, but this song will make their walls crumble.

The Social Network

Look, we can argue over whether or not the guy has any talent as an actor, but there are some facts that are inarguable: The Social Network was a fantastic movie all around and there was no better role for Timberlake to play than Sean Parker. I don’t think any other actor would have brought the right mix of charisma and “I want to hate him, but I don’t” smarm to the role, largely because the role so perfectly played on the love him/hate him dichotomy that is JT’s public persona.

The Singles Ladies Skit (Or any other SNL Skit)

You could slide any one of JT’s numerous winning Saturday Night Live sketches in here. Yes, the Digital Shorts he did with Andy Samberg are the stuff of legends, but let us not forget that every single one of his 5 times hosting the show can be counted as the highlights of any particular season. In years when the only reason people tuned into SNL was for the Digital Shorts, his episodes reliably churned out classic, hilarious sketches. When a guy can consistently make me laugh, well, hell, he’s going to get a lifetime pass.

The 2020 Experience - Justin Timberlake