When it comes to milestones in standup comedy, selling out Madison Square Garden ranks among the top, and certainly is the pinnacle when it comes to arena performances. According to the venue, there is no comprehensive list of comedians who have done so, but it is in the neighborhood of 15 — a “very small club,” as Matt Rife puts it.

Rife performed two sold-out shows at the Garden on July 18 and 19 as part of his Stay Golden tour. To commemorate the occasion, the venue presented him with a golden ticket. (You can see it on his Facebook page).

“If you think about the performers who have played that venue, [it’s] not just sports teams, but every single one of your favorite musicians,” he raves. “And it’s in New York City, where anybody can go see great shows all over the city seven nights a week, 365 days a year.”

Rife didn’t just perform to sell-out crowds at the Garden. At the age of 29 — he turns 30 in September — he became the youngest comedian to do so, as well as Billboard Boxscore’s top-grossing comedian for the month of June.

In the wake of those achievements, Rife — whose confidence is palpable — spoke to Billboard about the personal significance of the accomplishment, the lengths that is his female fans will go to get his attention, his reaction to Marc Maron‘s snipe at him and what he’s planning for his second act. (Hint: he’s a fan of Adam Sandler.)

You are the youngest comedian to sell out two nights at Madison Square Garden. Thoughts?

A lot of times these kinds of accomplishments and accolades are hard to process in the moment, because everything has been happening so fast. A lot of the shows have broken records at venues, and I go, “Oh, that’s really cool.” But not until two or three months later do I go, “Oh my god, wow, that happened.”

This was one of the few times that I got to be in the moment and acknowledge that, “Wow, I’m one of [very few] comedians to ever sell out Madison Square Garden.” For a standup comedian, the Garden is pretty much as big as it gets. I think only five comedians have ever played a stadium.

When you’re first starting out on an open mic, the dream is the Garden. So, to get to play it twice, sold-out, before the age of 30, it meant everything to me. I’m so grateful for my fans, my team, my friends and my family and everybody who has helped me get to this point right now. It feels very surreal.

I can share with you another milestone. You are Billboard Boxscore’s top-grossing comedian for June.

No way. That is awesome. It didn’t even feel like June was that busy of a month. That’s the craziest part.

Do you still grade your shows?

I try not to, but I do.

What grade would you give your Garden run?

Oh, that’s a tough one. I’m going to give them both an A — not A+, but A. I really had a good time at those shows, and I felt like the audience did as well. That’s not always the case. Sometimes I have a good time, and I feel like the crowd didn’t. Sometimes I feel like the crowd had a good time, and I didn’t.

I mentioned this onstage – I don’t know if it was a mistake or not but I did mean it — New York typically isn’t my favorite place to perform. In the past, I would say I’ve given my shows there at most a B or B+. So, with it being the Garden, I went in with very low expectations. I thought it could go terribly if people aren’t on board.

No pressure.

I really had a good time. They were some of the more fun shows of the entire tour so far.

The first night you were at the Garden, you brought out Jesse McCartney to close the show. Did he perform the second night as well?

No, just first night. He had a concert in, I think, Wisconsin the next day. He flew out just for that. He’s from [Westchester,] New York.

I love that era of music — the early 2000s — and I’m always playing him in the car. I hit him up, and I’m like, “Yo, I’m in your hometown. I’m just curious if you happen to be around the area and want to pop in and do the Garden.” He’s like, “I’m not in town, but I’d love to come by and give it a show.” He’s a fan of mine, so he enjoyed watching the show as well.

So, you didn’t know him prior to the show?

No, we had never met before. On a whim, I was like, “I’m just going to hit him up.” That’s the power of social media.

Speaking of social media, I was looking at your Facebook post on the Garden shows, and there were a lot of comments about the photo of the woman you’re with in the photo where you both have your backs to the camera. Are you willing to share?

Yeah, it’s my girlfriend, Mariah [Morse]. I don’t post a whole lot about my personal life on social media because people are absolutely insane, and at this point I try to distance your personal and professional life as much as possible.

It’s funny, in the photo you posted, your hands are just above a trash can in the hallway, and someone commented that you were carrying a bucket together.

Hilarious. I didn’t see that. This is why you don’t share stuff from your personal life. People’s speculations are always 100% wrong.

A New Yorker profile of you reported that, in past years, you did so many dates that you exhausted yourself.

Absolutely. This tour that we’re on this year and next is perfect middle ground for me. It’s a cycle of one weekend on, two weekends off. I did that for a balance of maintaining somewhat of a healthy life — but also, I hate not performing. As much as I tell myself, “I need a month break,” I cannot go more than two weeks without performing. I go stir crazy creatively, energetically.

This pace feels like a very healthy balance to me compared to doing 40-50 shows a month for the last two years prior to that. We did [hundreds of] shows the year prior which was a very unhealthy balance. That gets to a point where you’re so physically and mentally exhausted that it starts to feel like work.

But I was performing all around the world, and we’re selling out shows and breaking records at these revered theaters. Oftentimes I go back to those cities, and people are like, “We saw you last year.” I’m like, “I was here last year?” That’s so disappointing for myself. I lived some of these amazing memories, and I was too tired to even enjoy them.

When you do that many shows, do you start to get tired of the material in your set? And how do you deal with that?

Any comedian who says they never get tired of the material is either a liar or doesn’t perform enough. I try to be as present as possible. That’s why I don’t use a traditional microphone because it stops me from just crossing my arms and hiding behind a microphone. It forces me to walk around and use the stage. I like being as present as possible.There’s nothing worse than standing up there, and the words are leaving your mouth but your brain is thinking about something else.

You used a Billy Idol homage for your tour poster, and I read that your grandfather introduced you to his music.

Yeah, my grandpa put me on to classic rock as far back as I can remember. It’s still my favorite genre of music. Both of my last tours have been inspired by classic musicians. I did The Doors for my Problematic Tour poster. And then this one I did Billy Idol, and I actually dyed my hair blonde for it. I’ve never done anything like that before. Funny how the world works out. I actually got to work with Billy on the promo he did for his current tour. I had him sign my arm, and I went straight to the tattoo shop. So now I have Billy Idol tattoo on my arm.

And he did a promo for you. I don’t know if it was really your house, but says he’s been living there for days.

That was not my house. Yeah, we had five minutes to shoot my promo versus two days of shooting his. I was like, “You know what? F—k it. Let’s just see if we can do something on a phone real quick.” He’s the nicest, coolest guy. How he speaks, what he speaks about, the stories he had to tell. I’d love to play him in a biopic someday.

So, what happens after this tour ends?

We’re going to do a second half of this tour next year. The cities aren’t out yet. We’re going to tour about the same as we are this year. We’re going to do international as well. Then when that tour is over at the end of next year. I probably won’t do any prominent tours like this for a while. I might do a full month of shows, and I’ll still be doing spots around town in whatever city I’m popping around to.

But the commitment of knowing I have shows in November and it’s only February — I probably won’t do [again] that for a very long time. I’m really looking forward to transitioning over to film and television and we have a lot of projects in the works that I’m looking forward to moving my focus towards.

Right. By my count, you’re doing Marriage Material with Emma Roberts, Rolling Loud with Owen Wilson, the Netflix series about FTX, The Altruists, and The Escort, which is being directed by David Dobkin of Wedding Crashers fame. Did I miss anything?

That I’m allowed to speak on? No. We’ve got a couple of things with Netflix. Rolling Loud is coming out at the end of this year. The project with Emma Roberts, we had to postpone due to The Altruists schedule. It’s incredibly unfortunate. I’m such a huge fan of her and her work. The Altruists is an incredible limited series that’s highly anticipated, and I’m very excited to do something that is not comedy. It’s fully a drama, and an amazing opportunity to expand my skill set.

You’re playing Ryan Salame, who’s in prison for his role in that scandal. Have you met him?

I don’t know if I’m allowed to say this, but I am about to meet him. Fingers crossed. It’s interesting playing somebody else, because usually it’s up to the actor to make that character their own. But the directors and producers of The Altruists have been very clear that this is not a biopic series. We’re trying to get as close as possible to telling the true story about how this giant scandal happened and let people know the kind of craziness that went on.

It’s wild. I don’t know anything about the crypto world, and now that I’ve done the research, I’m like, “Oh my god.” I had no idea how many people were affected by this.

Are you looking to follow the career path of, say, Adam Sandler, where you’re going to primarily do TV and film and just do standup when you feel like it?

It’s hard to say. Life is going to take me in whatever direction it wants. But if I had it my way, yeah.

This is the weird thing about accomplishing as much as I have by 30, including the Garden. It’s like, “What do I do now?” It’s the most blessed predicament I can possibly dream of. As far as standup comedy, my dreams have come true. I know it wasn’t pure luck. I’ve worked my ass off, but it almost feels like I’ve hit the mark of, I could retire if I wanted to. I won’t stop performing until I die, but now I have to start thinking about, is there something I’m passionate about that’s new to me?  

Yeah, the goal would be film and television, primarily film. Then doing standup whenever I feel like it — and performing with my friends as much as I can. That’s one thing I love about Adam Sandler is, he’s always kept that tight-knit group around him.

I was looking at the Rolling Loud cast. You’ve got Sexxy Red, Ty Dolla $ign, Ski Mask the Slump God, and that Slizzy superstar Henry Winkler.

Oh, yeah man. This was a wild film experience. Working with Owen especially was a dream come true. You talk about the Mount Rushmore of comedic actors. He’s somebody who made me want to get into acting, and to learn from somebody like him was another dream come true. He’s the nicest, most talented guy. And the rest of the cast – they’re perfect for this movie. Everybody showed up to work. A lot of the times people who aren’t necessarily actors show up late because dedicating a day to acting is a pay cut for them. It’s not necessarily a priority to them. It’s just something where they’re like, “Oh, that would be cool to do.” That wasn’t the case with this movie.

What role you play?

I play Owen’s coworker who ends up at the festival with him and helps him find his lost son.

Are you in the music business in the movie?

No. He and I sell furniture. We have the most boring group of people.

Since this is Billboard, who are some of your favorite music artists?

I’m actually going to see some of them this coming weekend. Right now, I’m really listening to a lot of Red Clay Strays, Sam Barber, Zach Bryan, Morgan Wallen, Tyler Childers, Waylon Wyatt.

So, you’re a big country fan.

I really have moved towards that. To me the rap game has kind of fallen off. Classic rock is my No. 1. That’s always my go-to, what’s playing in the car most of the time. But I’m also a big hip-hop fan. J. Cole is probably my favorite artist of all time. But there’s currently no good hip-hop music. To me, hip-hop dropped the ball so bad. Country swooped in and took all that momentum. I really am feeling this new wave of country, folk, rock kind of blend. It’s beautiful. It really is music for the soul. Do you know who Sam Barber is?

I don’t.

Man, let me tell you. He’s a 22-year-old kid out of Montana who puts out some of the best music I’ve ever heard. I don’t know who hurt this kid, but his songwriting and his voice are absolutely incredible. A big shoutout to him.

Marc Maron took a swipe at you in 2023 calling you the “It Boy of s–tty comedy.” Any thoughts on that in retrospect?

There was never a beef. He was just being a crotchety old man and I’ve never even met the guy. I guarantee he’s never watched one of my shows, so if he wants to be bitter and angry that I get to live his dreams — yeah man, you’re kind of being a d–k to somebody who might have looked up to you. I used to love to watch Marc Maron standup.

I don’t have a beef with a single comedian. I am living my life, dude. What do I possibly have to complain about? I don’t hate on anybody. I don’t talk s–t about anybody. I’m just out here performing to the best of my ability. I play with my puppy and I hang out with my friends. I mind my own business and anybody who has a problem with that, it’s clearly an internal battle.

I was watching the “MILF & Cookies” video online, and I’ve got to know, what’s the wildest proposition you’ve gotten from one of your female fans? The “blowjob” tee shirt you are offered in that video was like, whoa.

People will come to shows with tee shirts all the time that say, like, “I’ll leave my husband for you” or “Matt Rife can offend me anytime.” And the propositions are all over the place, from sexual advances to gifting me jars of their hair.

Seriously? Jars of hair.

Oh, yeah. People are nuts.