Inspired by Ella Ceron and Rob Fee‘s bracket on the greatest Ludacris guest verse of all time, I teamed up with friend, musician and fellow pop-culture nerd Dana Wells, to develop a bracket to determine the best boy band ballad of the 90s/2000s. We tried our best to represent a variety of artists and ultimately decided to rank the below 16 songs:
1. I Swear – All 4 One vs. I Do (Cherish You) – 98 Degrees
2. I Want It That Way – Backstreet Boys vs. Truly, Madly, Deeply – Savage Garden
3. Too Close – Next vs. I’ll Make Love to You – Boyz II Men
4. Flying Without Wings – Westlife vs. All My Life – KC & JoJo
5. All or Nothing- O-Town vs. Back Here – BBMak
6. This I Promise You – *N Sync vs. She Will Be Loved – Maroon 5
7. Never Had a Dream Come True – S Club 7 vs. Crazy For This Girl – Evan and Jaron
8. Why I Love You – B2k vs. Walked Outta Heaven – Jagged Edge
90s Bracket Round 1
I Swear vs.
I Do (Cherish You)
D: I vaguely remembered “I Do”, but couldn’t think of any melody or lyrics. After watching the music video (which is basically a Zales commercial with more male hoop earrings and frosted tips than you can count), I realized why I didn’t remember it — it’s totally forgettable. So, despite Nick Lachey’s killer pecs and the ugly one proposing while his model girlfriend is in the bath, it’s got to go to the classic All-4-One hit ‘I Swear.’
E: For anyone who hasn’t watched this video, each band member proposes to a girl at some point, and all of the proposals are extremely questionable. The bath time proposal that Dana mentioned is super weird, and the proposal in the open-top convertible poses risks to both the ring itself and other drivers on the road. That said, the All-4-One video features the four band members physically chasing a girl all over New York City, so that’s not exactly normal, either. Weird videos aside, though, I’m gonna have to go with “I Swear” on this one—the song itself is better.
I Want It That Way vs.
Truly Madly Deeply
D: Not even a contest. ‘I Want It That Way’ mops the floor with the super melodramatic tears of ‘Truly Madly Deeply.’
E: Gonna agree with Dana on this one. ‘Truly, Madly, Deeply’ just screams “awkward teenage couples slow dancing,” while Backstreet Boys have always held a special place in the (shape of) my heart. Backstreet’s back, y’all.
Too Close vs. I’ll Make Love To You
D: This is a little tougher, mostly because I LOVE both of these songs and they’re both about sex, and sex will always be at its peak in 90s R&B form. I think this one has to go to ‘I’ll Make Love To You’ simply because ‘Too Close’ isn’t as truly a ballad, and when I think “boy band ballads,” I’d want to see the win go to Boyz II Men.
E: As much as I like the bluntness of ‘Too Close,’ Boyz II Men has staying power, so they advance.
Flying Without Wings vs. All My Life
D: If you didn’t know that ‘Flying Without Wings”’ was originally released in 1999 by British boy band Westlife and that American Idol winner Ruben Studdard’s version was a cover, you are probably (like we are) American. This is a great song by a quintessential British boy band, but I have to go with my heart and say ‘All My Life’ because THAT song is amazing.
E: I remember always seeing posters of Westlife in my J-14, but never remembering to actually listen to their music. This song is actually pretty cute and the guys are good singers (though it looks like nobody told them you’re allowed to leave the recording studio when filming a music video). However, ‘All My Life’ is such a pretty song, I love the piano riff and dudes can SANG. K-Ci & JoJo win this round.
2000s Bracket Round 1
All or Nothing vs.
D: Regarding pure nostalgia, I’m going to say ‘All or Nothing.’ That song just screams middle school dances and having to stay a walkie-talkie length from my dance partner.
E: I really do like ‘Back Here,’ but ‘All or Nothing’ made more of a lasting impression on our 11-year-old hearts. They move on.
This I Promise You vs.
She Will Be Loved
D: ‘She Will Be Loved’ is a nice ballad, but when you compare their boy band status against *N Sync, Maroon 5 just can’t compete. This goes to ‘This I Promise You,’ hands down.
E: Agreeing with Dana here. With only one singer, I hardly consider Maroon 5 a boy band. Plus, *N Sync’s ugly sweater game is (unintentionally) on point in this video.
Never Had A Dream Come True vs. Crazy For This Girl
D: ‘Never Had A Dream Come True’ was my first “song” with my middle school boyfriend (we couples’ skated to it at the roller rink — true story) and we all know that there ain’t no party like an S Club Party, but since S Club is TECHNICALLY not a boy band, I have to give this round to adorable Jewish twins Evan and Jaron.
E: Maybe I’m a little bitter here because Dana had a cool boyfriend in middle school, but Evan and Jaron kill it in ‘Crazy For This Girl.’ I still rock this song on the regular. They bring more to the table than all seven S Club members. Plus, there’s the whole technicality issue of including a band with four girls. Evan and Jaron move to the next round.
Why I Love You vs.
Walked Outta Heaven
D: Full disclosure, I didn’t remember either song until I listened to them. The Jagged Edge song is featured on Now 14, while ‘Why I Love You’ was a go-to slow dance song at 8th grade parties. For me, ‘Why I Love You’ takes this round because it is actually a KILLER track with amazing chord changes that are unexpected and creative, and a hook I could sing all day.
E: I didn’t remember either of these songs either — how did we find these again? Does someone need to audit our bracket? I definitely prefer the faster-paced songs from both of these bands, but the B2K song is much catchier and they have actual dance moves, whereas Jagged Edge just kind of sit there in oversize jerseys.
90s Bracket Round 2
I Swear vs. I Want It That Way
E: This is tough because I feel like these are both poster children for 90s boy band slow jams in the R&B and pop markets, respectively. Truthfully, though, ‘I Swear’ was before my time, and whenever I hear that song, I just think of that opening scene from Just Friends when fat-suit Ryan Reynolds sings this with a retainer-induced lisp. Plus, 9-year-old me would be super disappointed if Backstreet Boys lost this round.
D: Maybe it’s because ‘I Swear’ came out before my time listening to boy band pop songs, or possibly because of the aforementioned Just Friends scene, but it just can’t touch the BSB classic. I mean, seeing the Backstreet Boys sing nonsensical lyrics so passionately? Gold.
I’ll Make Love To You vs.
All My Life
E: The Boy Band Constitution doesn’t state any rules about a minimum number of members to be considered for the Best Boy Band Slow Jam title, but I would feel a little weird with a duo in our final four. Boyz II Men takes it.
D: I’m going to level with you here: I actually think that ‘All My Life’ is a better song than ‘I’ll Make Love To You.’ But we’re not judging “best song” here. We’re judging the best boy band ballad. And with that criteria in mind, this round goes to Boyz II Men.
2000s Bracket Round 2
All or Nothing vs. This I Promise You
E: So, I’m definitely NOT watching O-Town music videos on YouTube at my office, but if I was, I’d notice that the band looks like a group of five townies (O-Townies?), which I guess they technically are, since they got their start on Making the Band. Still, their sound is less “timeless slow jam” and more “construction workers trying to pick up divorced moms at Applebee’s Karaoke Night.” I ain’t down with that. *N Sync moves forward.
D: My first arena concert was *N Sync at the MCI Center in D.C. They did a full-band cover of ‘That Thing You Do’ and then were attached to pulleys on the ceiling and flew over the audience. O-Town can’t compete. Sorry, Ashley Parker Angel. You and that guy with the dreads can go cry in the corner.
Crazy For This Girl vs. Why I Love You
E: As much as I love the mensch’s that are Evan and Jaron, B2K really dominated the R&B boy band market at this time, and their video has all of the boy band staples — matching leather jackets, choreographed dance moves, and the token ugly guy (sorry Raz-B). I have to give this round to B2K.
D: Seriously, if you don’t know ‘Why I Love You,’ go listen to it now. SO GOOD. I also just realized that Marques Houston is in this video (which makes sense because he’s Omarion’s cousin)…GO HOME, ROGER! This isn’t your band! Also, Naya Rivera from Glee is in it? I’m confused. Whatever, it’s great.
90s Bracket Round 3
I Want It That Way vs.
I’ll Make Love To You
D: These next two are more difficult because they are drastically different bands, songs, and genres — ah, the diversity of boy band pop. In this case, I’m going to have to refer to the fact that ‘I Want It That Way’ just speaks to my soul in a way that ‘I’ll Make Love To You’ doesn’t. Maybe because “I’ll Make Love To You” came out when I was a child, and I didn’t understand it. You know what I did understand? Singing in an airplane hangar, oversized jackets, and Brian Litrell’s cheekbones.
E: True that. Us 90s kids were too young to appreciate ‘I’ll Make Love To You…’ but we were just old enough to appreciate AJ’s collection of bad hats.
2000s Bracket, Round 3
This I Promise You vs.
Why I Love You
D: I’ve made my love of ‘Why I Love You’ clear in the last few rounds, but one thing is undeniable: people still care about *N Sync (or, as I’ve recently seen them called, Justin Timberlake and Friends), and not as many people still remember B2K. JT&Friends, this round is yours.
E: As much as ‘Why I Love You’ bumps, when I think of 2000s boy bands, B2K really isn’t a top-of-mind result — *N Sync has more staying power; thus, they advance.
I Want It That Way vs.
This I Promise You
E: I feel like I just shaded the entire boy band R&B market since they aren’t at all represented in the final round. But, given our sound methodology, I know *N Sync and BSB are here fair and square. As much as I want to be Switzerland in the war between *N Sync and BSB, it’s time to pick a side…and I’m ultimately going to go with Backstreet. The Backstreet Boys really utilize the airport setting of their music video, meanwhile most of the *N Sync video looks like it was shot in the forest from Lord of the Rings. In terms of vocals, four of the five BSB members have solos, whereas *N Sync takes the “strength in numbers” approach literally and basically just throws three extra bodies alongside JT and JC. Lastly, *N Sync just stands around in their video, whereas The Boys (can I say that?) have some sweet choreography that I’m totally going to teach myself after work today. Therefore, I declare ‘I Want It That Way’ The Best Boy Band Slow Jam.
D: Look, I think we all knew this was going to end up as an *N Sync vs. BSB final two, even if it wasn’t planned that way (and, it wasn’t — this I promise you, even if I wanted it that way. UGH I’M THE WORST.) I’ll be real: I like *N Sync more than I like BSB. Always have, always will. The BSB guys took themselves too seriously, and I wanted to hang out with JT, JC, Joey, Chris, and even Lance (somewhat.) But that’s not what this is about. This is about the BEST BOY BAND BALLAD. Unfortunately, *N Sync had great upbeat songs, but not amazing ballads. BSB had SO MANY good ballads that we actually considered doing a BSB-only bracket. It’s a tough call, but this bracket goes to BSB and ‘I Want It That Way.’
E: Do they get a prize?
D: Our sympathy for having to join New Kids on the Block. (Too soon?)