The Stanley Cup will be in the building tonight in Boston, with the Chicago Blackhawks one win away from claiming the championship. And that means it’s time to get excited about one of the highlights of the NHL season: Watching commissioner Gary Bettman struggle through presenting the Cup.

In the years since Bettman’s debut as the Stanley Cup presenter, the ceremony has evolved into one of the most awkward traditions in all of sports. Bettman fidgets, the crowd boos, the posed photo takes way too long, and the winning captain fakes a smile while he waits for Bettman to just let go of the Cup and hit the bricks.

Calls for Bettman to step aside and let somebody else do the honors have reached the point where it’s practically a consensus. But he’s made it clear that he has no intention of doing so, and he will be back out there again this year.

All of which is great news for fans of unintentional comedy. So to mark the occasion, I thought it would be fun to go through all 20 years of Bettman’s reign (there are 19 presentations total, thanks to one year lost to a lockout) and rank them in order of awkwardness.

We’ll be using the following criteria:

Crowd Response: The more hostile the better. Unfortunately, not every video clip I found includes Bettman’s introduction, but we’ll do our best to piece everything together.

Cup Handoff: A combination of factors, including: How disgusted does the captain seem to be by Bettman’s presence? How long does it take them to get the photo right? Can they figure out which hand goes where? Is Steve Yzerman involved? (That last one turns out to be important.)

Bettman Awkwardness: A catchall, and the most important category. We’re looking
at everything from hair to wardrobe to random gesticulation to attempted one-liners to his level of flusteredness, which I don’t think is a word but should be.

Overall: The combined level of overall awkwardness. Not necessarily an average.

So here we go … 20 years’ worth of presentations, ranked in order from the least to the most awkward.

19. 2001, Colorado Avalanche

The Scene: Pepsi Center in Denver

Captain: Joe Sakic, who creates one of the most memorable moments in recent NHL history when he hands it off directly to Ray Bourque.

Crowd Response: 1/10. This was all about Bourque. They’re not booing anyone.

The Handoff: 1/10. Even Bettman is smart enough to get this over with quickly.

Bettman Awkwardness: 4/10. You can tell he’s feeling the moment, because he’s doing this weird thing with his hand that makes him look like he’s attempting a bad impersonation of Tom Jones.

Overall: 1.8/10. Ray Bourque, you ruin everything.

18. 1996, Colorado Avalanche

The Scene: Miami Arena

Captain: Joe Sakic

Crowd Response: 2/10. This was the first time Bettman had to present the Cup to a road team. But the Florida crowd takes it pretty easy on him, which is understandable, given they just sat through a triple-overtime 1-0 game and are probably all sleeping.

The Handoff: 2/10. By Bettman standards, this one is relatively flawless. The photo pose probably goes a little long, but that’s nit-picking.

Bettman Awkwardness: 3/10. Not much here, though he does break out the patented Bettman crazy eyes when he calls Sakic over.

Overall: 2.5/10. Like everything else about the 1996 Cup final, this was completely forgettable.

17. 2004, Tampa Bay Lightning

The Scene: St. Pete Times Forum in Tampa

Captain: Dave Andreychuk

Crowd Response: 1/10. The Lightning fans are in a good mood, even cheering the Flames.

The Handoff: 5/10. Andreychuk hugs Bettman, which isn’t really Bettman’s fault but still kills me.

Bettman Awkwardness: 3/10. He’s doing the Tom Jones thing again.

Overall: 3.4/10. A weak effort. Between this and 1996, we have all the proof we need that NHL hockey will never work in the state of Florida.

16. 2000, New Jersey Devils

The Scene: Reunion Arena in Dallas

Captain: Scott Stevens

Crowd Response: 3/10. There are some mild boos when he takes the ice, but they don’t let him have it too badly (despite a Dallas PA announcer who sure sounds like he’s subtly trying to egg them on). And when he starts flattering the Stars, the crowd buys it hook, line, and sinker.

The Handoff: 2/10. Nice and quick. Which it probably had to be, since after a rambling speech where Bettman decides to mention every single person in the building, the preseason was about to start.

Bettman Awkwardness: 6/10. Seriously, someone hire this guy an editor. Also: “When you think of … doing the right thing, you think of Lou Lamoriello.” Sure you do, Gary.

Overall: 4.2/10. As we’ll see, it was a huge break for Bettman that this game was in Dallas instead of New Jersey.

15. 2012, Los Angeles Kings

The Scene: Staples Center in L.A.

Captain: Dustin Brown

Crowd Response: 3/10. After a streak of four consecutive years of presenting the Cup to the visitors, Bettman finally gets to give it to a home team. And for the first time in the post-lockout era, he gets a fairly positive response. Lots of hockey fans were outraged at this, and acted as if the L.A. fans had failed some sort of test. But they’d just seen their team win their first Cup after four decades, so maybe we should cut them some slack.

The Handoff: 7/10. Bettman greets Brown by grabbing him by the arm, probably to prevent him from reacting to the contact by instinctively diving. From there, the Kings captain can’t figure out which way to hold the Cup, and Bettman is so disgusted he nearly knocks him over with it.

Bettman Awkwardness: 4/10. He seems thrown off by the positive reception, almost as if he had some good material ready to go and now he can’t use it. It’s also fun to see how annoyed he gets when the PA guy goes too long on his Conn Smythe introduction.

Overall: 4.6/10. Not bad, but without question the weakest effort of the salary-cap era.

14. 1999, Dallas Stars

The Scene: Marine Midland Arena in Buffalo

Captain: Derian Hatcher

Crowd Response: 6/10. There are definitely some audible boos for Bettman, and everyone else whose name is announced. But considering the circumstances, the Buffalo crowd is actually remarkably restrained.

The Handoff: 3/10. It seems fairly well-done, though it’s a little tough to tell thanks to some shaky work by our cameraman, Abraham Zapruder.

Bettman Awkwardness: 5/10. I think this is the first year Bettman deploys what would become his traditional road strategy: the preemptive “congratulate the losing team in an effort to win over the crowd” moment. It works, briefly.

Overall: 5.1/10. Given the potential for disaster with the way the winning goal played out, this went remarkably well.

13. 1997, Detroit Red Wings

The scene: Joe Louis Arena in Detroit

Captain: Steve Yzerman

Crowd Response: 1/10. We don’t actually get to see Bettman’s full intro in this clip, but this is the Red Wings’ first Cup in 42 seasons. The fans in Detroit are way too happy to boo. Don’t worry, they’ll get more chances down the road.

The Handoff: 6/10. Bettman and Yzerman both make the rookie mistake of grabbing the top of the Cup with their front arms, blocking their faces. Bettman recovers quickly. Yzerman does not.

Bettman Awkwardness: 8/10. He waves his finger menacingly during a short speech about Yzerman that’s so heartwarming that the Wings captain decides to randomly start picking garbage off the ice rather than pay attention.

Overall: 5.4/10. Almost entirely for Yzerman’s bumbling performance. Which, as we’ll find out, is not even close to the best he can do.

12. 2008, Detroit Red Wings

The Scene: Mellon Arena in Pittsburgh

Captain: Nicklas Lidstrom

Crowd Response: 8/10. Pretty much start-to-finish boos.

The Handoff: 1/10. It’s basically perfect, because god forbid Nicklas Lidstrom do one thing wrong in his entire career.

Bettman Awkwardness: 6/10. The boos clearly have Bettman rattled, as he spends the entire time with a look on his face that says Man, how many lotteries does a guy have to rig to get a cheer around here?

Overall: 6.1/10. Needs more Yzerman.

11. 1994, New York Rangers

The Scene: Madison Square Garden in New York

Captain: Mark Messier

Crowd Response: 0/10. The Rangers have just won their first Cup in 54 years, so MSG is euphoric. Bettman wouldn’t have been booed here if he’d walked out wearing a Red Sox cap and a Denis Potvin jersey.

The Handoff: 9/10. Messier is downright giddy, but Bettman adamantly refuses to let go of the Cup. For some reason, this makes Messier start laughing like a Bond villain.

Bettman Awkwardness: 7/10. The early ’90s hair is pretty ridiculous, and Bettman is forced to halfheartedly wave Messier over when the captain fails to show up on time.

Overall: 6.3/10. I miss Bettman’s pre-corporate haircut so much.

10. 2002, Detroit Red Wings

The Scene: Joe Louis Arena in Detroit

Captain: Steve Yzerman

Crowd Response: 8/10. You don’t really get a sense for it on the video, but they’re clearly giving Bettman a rough time as he takes to the ice because he hilariously breaks out his Patrick Roy impression.

The Handoff: 3/10. This is the third handoff in the Bettman-to-Yzerman trilogy and the only one that goes relatively smoothly, probably because Yzerman brings his daughter along to tell them what to do.

Bettman Awkwardness: 7/10. He seems oddly peevish early on, opening with the quasi-joke “I come bearing gifts.” By the time the Cup arrives, he goes into full suck-up mode with lines about Hockeytown and inducting the entire team into the Hall of Fame.

Overall: 6.8/10. If Yzerman had brought his A-game, this could have been an all-time classic.

9. 2010, Chicago Blackhawks

The Scene: Wachovia Center in Philadelphia

Captain: Jonathan Toews

Crowd Response: 9/10. They’re booing pretty much constantly. Although in fairness, this is Philadelphia, so they may not even know Bettman is there.

The Handoff: 3/10. I love the noise Toews makes when he skates away with the Cup. This really has nothing to do with Bettman, but I wanted to mention it.

Bettman Awkwardness: 6/10. At this point, Bettman had basically accepted the fact he was going to get booed every time. He even works in a sarcastic dig at “the passion of Philadelphia fans” during the Conn Smythe presentation.

Overall: 7.1/10.

8. 2009, Pittsburgh Penguins

The Scene: Joe Louis Arena in Detroit

Captain: Sidney Crosby

Crowd Response: 9/10. By now the “Boo Bettman” tradition has been firmly established. Detroit fans pick up where Pens fans left off the year before, only louder.

The Handoff: 3/10. Pretty smooth, though I’d love to know what their little conversation was about at the beginning.

Bettman Awkwardness: 6/10. Almost two decades into the job and Bettman still can’t figure out what to do with his free hand. This time he decides to go with “continually attempt to execute a Five Point Palm Exploding Heart Technique on the trophy stand.”

Overall: 7.3/10. Nice playoff beard, Crosby.

7. 1995, New Jersey Devils

The Scene: Brendan Byrne Arena in East Rutherford

The Captain: Scott Stevens

Crowd Response: 9/10. It’s a pretty solid rain of boos right up until Bettman announces Claude Lemieux’s name. Rule of thumb: If you need to name-drop Claude Lemieux to get a more positive response, the audience hates you.

The Handoff: 7/10. For some reason, Bettman is cradling the Cup like it’s an oversized infant. He hands it over and then turns to leave, marking the only known time that anyone took their eyes off Stevens without immediately taking a shoulder pad to the temple.

Bettman Awkwardness: 3/10. After two years of looking like an extra from an episode of Friends, this season was the debut of the traditional Bettman haircut that has remained exactly the same ever since. Such a devastating loss.

Overall: 7.5/10. The Devils’ 1995 championship created two trends that would last for decades — stifling defensive hockey that made the NHL borderline unwatchable, and an arena full of people booing Gary Bettman. Let’s call it even.

6. 2007, Anaheim Ducks

The Scene: Honda Center in Anaheim

Captain: Scott Niedermayer

Crowd Response: 7/10. Solid boos when he makes his first appearance. Not quite New Jersey level, but a strong showing.

The Handoff: 8/10. After botching the handshake, Niedermayer goes to yank the Cup away prematurely only to have Bettman stubbornly hold on. This whole exchange is fantastic.

Bettman Awkwardness: 6/10. He goes all @prodigalsam on us by recycling his “bringing a gift” line from 2002.

Overall: 8.2/10. A strong effort by the Anaheim crowd, unlike some other California teams I could mention.

5. 2003, New Jersey Devils

The Scene: Continental Airlines Arena in New Jersey

Captain: Scott Stevens

Crowd Response: 9/10. Picking up where it left off in 1995, the crowd lets Bettman have it with both barrels. They’re actually pretty tepid when he’s introduced, but they don’t react well to the Conn Smythe going to a player from the losing team, and by the time the Cup arrives, they’re booing him mercilessly. Remember, these fans just saw their team win. If the Ducks had pulled off the upset, Bettman was getting pelted by rotten fruit.

The Handoff: 4/10. Relatively smooth, other than Bettman having to give Stevens the “I’m going to pat you on the back a little too hard because you’re standing in the wrong spot” move.

Bettman Awkwardness: 8/10. Between the boos, and Bettman’s obvious annoyance when the sound guy forgets to cut off We Are the Champions so he can talk, this was a rough outing.

Overall: 8.5/10. Devils fans are the best.

4. 1998, Detroit Red Wings

The Scene: MCI Center in Washington, D.C.

Captain: Steve Yzerman

Crowd Response: 3/10. We don’t actually get to see Bettman’s introduction, but given that the crowd cheers Yzerman I’m guessing they weren’t in much of a booing mood.

The Handoff: 10/10. One of the best handoff moments of all time. Yzerman goes to the wrong spot, so when Bettman dramatically turns around to give him the Cup Yzerman isn’t there. They end up facing in the wrong direction, posing for a photographer they can’t find, until eventually a visibly annoyed Bettman has to order Yzerman to turn around while still maintaining a manically forced grin. The whole thing is poetry.

Bettman Awkwardness: 8/10. Bettman builds up some goodwill with a nice tribute to Vladimir Konstantinov and Sergei Mnatsakanov, then ruins it with a “Steve Yzerman, let’s do it again” line that makes everyone feel vaguely uncomfortable.

Overall: 8.6/10. We really need to find a way for Yzerman to be involved in every Cup presentation.

3. 1993, Montreal Canadiens

The Scene: Montreal Forum

Captain: Guy Carbonneau, but the Cup actually gets passed to Denis Savard wearing a suit.

Crowd Response: 4/10. There’s an audible smattering of boos when he’s introduced, though he wins them over once he starts speaking French.

Cup Handoff: 8/10. This was Bettman’s first attempt, so he doesn’t quite have it down pat yet, and Carbonneau throws a wrench into things by inviting half the team over. Bettman is surrounded and seems unsure what to do. At the end, it kind of looks like Jacques Demers has to lean in and tell him that it’s time to get lost.

Bettman Awkwardness: 11/10. Where to begin … The hair? The tie? The way he walks onto the ice like a sullen teenager? Him trying to speak French while reading the words phonetically off what appears to be a postage stamp?

Overall: 8.9/10. Beaucoup de le cringing. Bettman’s debut set the bar for future presentations very, very high.

2. 2011, Boston Bruins

The Scene: Rogers Arena in Vancouver

Captain: Zdeno Chara

Crowd Response: 11/10. This one is just brutal. The fans not only boo him mercilessly, but at least a few actually to try to pelt him with bottles. This is an early-NWO era level of heat. Remember, many of these fans left the building and immediately rioted. They are not happy.

The Handoff: 6/10. Bettman actually does a reasonably decent job, once you get past the fact that he’s dodging garbage and has to give the Cup to a guy who’s roughly three feet taller than he is.

Bettman Awkwardness: 8/10. There’s that Tom Jones hand again. Honestly, Bettman is getting booed so badly here that you almost feel sorry for him. Almost. As an added bonus, he completely leaves Tim Thomas hanging when the Bruins goalie clearly has no idea what to do with the Conn Smythe Trophy.

Overall: 9.3/10. This one is legitimately hard to watch.

1. 2006, Carolina Hurricanes

The Scene: RBC Center in Raleigh

Captain: Rod Brind’Amour

Crowd Response: 7/10. The boos aren’t all that bad, but this section comes with an asterisk: This was the year after a lockout wiped out the 2004-05 season, so the NHL blatantly cheated and had the Carolina PA guy announce the Conn Smythe while Bettman slipped in without an actual introduction. Smart move. He still gets booed, but nowhere near as badly as he could have.

The Handoff: 11/10. A total disaster. First, Brind’Amour shows up early, leading Bettman to scold him by yelling “I’m almost done” into a live microphone. Then, when Bettman finally finishes rambling on, Brind’Amour takes the Cup rather than waiting for the commissioner to give it to him. He just rips it out of Bettman’s hands and immediately starts making out with it. This is one of the greatest hockey moments of all time.

Bettman Awkwardness: 10/10. Seriously, Rod Brind’Amour needs to be in the hockey Hall of Fame just for that 15-second sequence. I’m amazed Bettman was able to resist the urge to physically attack him. Also, at some point during the lockout, someone clearly told Bettman to just keep his free hand in his pocket, but he can’t quite pull it off — the hand keeps escaping for a few seconds of pointing.

Overall: 9.8/10. You’re the man, Rod.