Music & Concerts
As Madonna and the Billboard Hot 100 turn 60, challenges ahead for both
Despite record chart stats and decades of hits, her traction has steadily eroded in recent years


Madonna in her ‘Rebel Heart’ era in 2015. The singer turns 60 next week. (Photo courtesy Live Nation)
Interestingly Madonna and the Billboard Hot 100 chart are both turning 60 this month and the industry Bible has announced she’s the all-time chart queen with 57 entries and 12 no. 1 hits (Mariah Carey and Janet Jackson are in second and third place respectively).
The numbers are impressive — Madonna holds the record for most top 10 hits of all acts with 38 and she’s had 46 no. 1 hits on the Billboard Dance Club Songs chart, more chart toppers than any act has ever accumulated on any Billboard chart.
That’s the good news. The bad news is that despite consistently putting out solid material in the last 10-15 years, her chart dominance has waned considerably with only one of her last seven singles even cracking the Hot 100 (“Bitch I’m Madonna” made it to no. 84 in 2015), an unthinkable track record compared to her ‘80s and ‘90s heyday. Her last U.S. top-10 hit was “Give Me All Your Luvin” in 2012; her last no. 1 was “Music” in 2000.
But how much of it is — as Madonna has claimed — ageism? Do the men (Springsteen, Paul McCartney, U2) with new material fare any better than women (Stevie Nicks, Cher, etc.)? The short answer is not really. The only time McCartney has had hits in the last 30 years were his high-charting collaborations with Kanye West, Rihanna, et. al. (“FourFiveSeconds made it to no. 4 and “All Day” to no. 15, both in 2015.) When’s the last time you heard a new U2 song on the radio?
And are the numbers even relevant, as the Washington Post has suggested, now that Billboard records are constantly being broken as the agency continues shuffling its methodology to factor streaming into the popularity equation?
One particularly eyebrow-raising shattered record happened last year when Nicki Minaj passed Aretha Franklin for most Billboard Hot 100 entries of any female artist, amassing 73 since 2010 alone. She pulled off this astounding feat because she’s such a ubiquitous guest artist (occasionally with Madonna): 32 of her entries are as lead artist; she’s “featured” on the other 44. Just based on number of entries among women, Madonna comes in fifth behind Rihanna, Taylor Swift, Franklin and Minaj. She ranks higher overall based on her actual numbers (i.e. Madonna’s singles haver generally charted higher than Franklin’s, Minaj’s etc. so she has more overall chart heft despite fewer entries).
Fans have been concerned as far back as 2006 when they launched an “End the Madonna on U.S. radio Boycott” aimed at Clear Channel Communications after her “Confessions” singles failed to generate much interest. It hasn’t improved. Madonna herself cried foul in 2015 when Great Britain’s BBC Radio 1 declined to play her then-new single “Living for Love.” And in a 2016 speech in which she was named Woman of the Year at a Billboard Women in Music awards ceremony, she said in the world of music, “To age is a sin. You will be criticized, you will be vilified and you will definitely not be played on the radio.”
That pop music and the Hot 100 has always pretty much been a young person’s game is a fairly accepted music industry truism. Look at any female pop singer going back to the days of Connie Francis (53 Hot 100 entries), Brenda Lee (48) or Dionne Warwick (56) — none of them were having major hits into their 50s and 60s. Despite a major comeback in her 40s, Tina Turner’s chart power slipped as she got older. Even Cher’s 1998 hit “Believe,” often cited as an example of what’s possible for older women artists, was a bit of a fluke. When it hit no. 1 on the Hot 100 in 1999, she was 52 and became the oldest woman to have a no. 1 hit. But that was 20 years ago and only two of the 16 singles she’s released since then have even cracked the Hot 100, the highest (“Strong Enough”) at no. 57. Like Madonna, she’s fared much better on the dance chart.
Pink, 38, told the New York Times last year while promoting her latest release “Beautiful Trauma” she knew her days on the chart were limited (she’s had 23 top 40 hits).
“I had the whole sit-down, you know: ‘Just be prepared — they don’t play girls over 35 on top 40 radio,’” she told the Times. “There are exceptions but they’re songs, not artists — unless you’re Beyonce.”
Thus far Madonna appears fairly undeterred. With “MDNA” in 2012 and “Rebel Heart” in 2015, she’s kept to a fairly regular release schedule. She’s teased new material on social media and appears to still enjoy making new music and live performance. She wowed the crowd in May with an elaborate performance at the Met Gala performing “Like a Prayer” at the “Fashion and the Catholic Imagination” event (right up her alley thematically).
But how long will Madonna feel like going back to the well if this law of diminishing returns continues as it’s likely to? Sure, Madonna does lots of things — she writes, acts (not so much anymore) and directs, but what is she supposed to do when the thing she clearly does best no longer has a place in pop culture? One might argue we don’t expect our sports legends to keep up the pace and records they set in their prime but writing, recording and releasing a hit single doesn’t require one to be at peak physical ability. It could — in theory — happen at any age.
The situation is somewhat exacerbated by Madonna’s own restlessness. Obviously from her comments, the way she constructs her shows, even down to the arrangements of her old hits live, she’d never be happy on a gravy-train nostalgia-fest which Cher, Dionne Warwick, Diana Ross and most veteran acts are perfectly fine with. They paid their dues over many decades — now is their times to phone it in, never break much of a sweat and collect the dough. Madonna would be bored out of her mind with that approach.
Her tours are still massive extravaganzas that sell out all around the world (she’s the top-grossing female touring artist of all time) but she’ll never expand her considerable fan base into younger generations with zero radio support. Outside of touring, there’s nothing comparable in pop music for the way actresses like Jessica Lange, Jodie Foster, Kathleen Turner and Glenn Close (Meryl is, of course, in a league of her own, no pun intended) have managed to keep the creative fires burning with TV, directing and stage work. Younger audiences still have ways to discover them.
It will be interesting to see how Madonna — and the Pinks and Beyonces of the world after her, for their time will surely come as well — tackles this conundrum in the years to come.
Music & Concerts
Underdog glorious: a personal remembrance of Jill Sobule
Talented singer, songwriter died in house fire on May 1

I’ve always prided myself on being the kind of music consumer who purchased music on impulse. When I stumbled across “Things Here Are Different,” Jill Sobule’s 1990 MCA Records debut album on vinyl in a favorite Chicago record store, I bought it without knowing anything about her. This was at a time when we didn’t have our phones in our pockets to search for information about the artist on the internet. The LP stayed in my collection until, as vinyl was falling out of fashion, I replaced it with a CD a few years later.
Early in my career as an entertainment journalist, I received a promo copy of Jill’s eponymous 1995 Atlantic Records album. That year, Atlantic Records was one of the labels at the forefront of signing and heavily promoting queer artists, including Melissa Ferrick and Extra Fancy, and its roster included the self-titled album by Jill. It was a smart move, as the single “I Kissed A Girl” became a hit on radio and its accompanying video (featuring Fabio!) was in heavy rotation on MTV (when they still played videos).
Unfortunately for Jill, she was a victim of record label missteps. When 1997’s wonderful “Happy Town” failed to repeat the success, Atlantic dumped her. That was Atlantic’s loss, because her next album, the superb “Pink Pearl” contained “Heroes” and “Mexican Wrestler,” two of her most beloved songs. Sadly, Beyond Music, the label that released that album ceased to exist after just a few years. To her credit, the savvy Jill had also started independently releasing music (2004’s “The Folk Years”). That was a smart move because her next major-label release, the brilliant “Underdog Victorious” on Artemis Records, met a similar fate when that label folded.
With her 2009 album “California Years,” Jill launched her own indie label, Pinko Records, on which she would release two more outstanding full-length discs, 2014’s “Dottie’s Charms” (on which she collaborated with some of her favorite writers, including David Hadju, Rick Moody, Mary Jo Salter, and Jonathan Lethem), and 2018’s stunning “Nostalgia Kills.” Jill’s cover of the late Warren Zevon’s “Don’t Let Us Get Sick” on “Nostalgia Kills” was particularly poignant as she had toured with him as an opening act.
Jill was a road warrior, constantly on tour, and her live shows were something to behold. My first interview with Jill took place at the Double Door in Chicago in early August of 1995, when she was the opening act for legendary punk band X. She had thrown her back out the previous day and was diagnosed with a herniated disc. To be comfortable, she was lying down on a fabulous-‘50s sofa. “I feel like I’m at my shrink’s,” she said to me, “Do you want me to talk about my mother?”
That sense of humor, which permeated and enriched her music, was one of many reasons to love Jill. I was privileged to interview her for seven of her albums. Everything you would want to know about her was right there in her honest lyrics, in which she balanced her distinctive brand of humor with serious subject matter. Drawing on her life experiences in songs such as “Bitter,” “Underachiever,” “One of These Days,” “Freshman,” “Jetpack,” “Nothing To Prove,” “Forbidden Thoughts of Youth,” “Island of Lost Things,” “Where Do I Begin,” “Almost Great,” and “Big Shoes,” made her songs as personal as they were universal, elicited genuine affection and concern from her devoted fans.
While she was a consummate songwriter, Jill also felt equally comfortable covering songs made famous by others, including “Just A Little Lovin’” (on the 2000 Dusty Springfield tribute album “Forever Dusty”) and “Stoned Soul Picnic” (from the 1997 Laura Nyro tribute album “Time and Love”). Jill also didn’t shy away from political subject matter in her music with “Resistance Song,” “Soldiers of Christ,” “Attic,” “Heroes,” “Under the Disco Ball,” and the incredible “America Back” as prime examples.
Here’s something else worth mentioning about Jill. She was known for collaboration skills. As a songwriter, she maintained a multi-year creative partnership with Robin Eaton (“I Kissed A Girl” and many others), as well as Richard Barone, the gay frontman of the renowned band The Bongos. Jill’s history with Barone includes performing together at a queer Octoberfest event in Chicago in 1996. Writer and comedian Julie Sweeney, of “SNL” and “Work in Progress” fame was another Chicago collaborator with Sobule (Sweeney lives in a Chicago suburb), where they frequently performed their delightful “The Jill and Julia Show.” John Doe, of the aforementioned band X, also collaborated with Jill in the studio (“Tomorrow Is Breaking” from “Nostalgia Kills”), as well as in live performances.
On a very personal note, in 2019, when I was in the process of arranging a reading at the fabulous NYC gay bookstore Bureau of General Services – Queer Division, I reached out to Jill and asked her if she would like to be on the bill with me. We alternated performing; I would read a couple of poems, and Jill would sing a couple of songs. She even set one of my poems to music, on the spot.
Jill had an abundance of talent, and when she turned her attention to musical theater, it paid off in a big way. Her stage musical “F*ck 7th Grade,” a theatrical piece that seemed like the next logical step in her career, had its premiere at Pittsburgh’s City Theatre in the fall of 2020, during the height of the pandemic. The unique staging (an outdoor drive-in stage at which audience members watched from their cars) was truly inspired. “F*ck 7th Grade” went on to become a New York Times Critic’s pick, as well as earning a Drama Desk nomination.
In honor of the 30th anniversary of Jill’s eponymous 1995 album, reissue label Rhino Records is re-releasing it on red vinyl. Jill and I had been emailing each other to arrange a time for an interview. We even had a date on the books for the third week of May.
When she died in a house fire in Minnesota on May 1 at age 66, Jill received mentions on network and cable news shows. She was showered with attention from major news outlets, including obits in the New York Times and Rolling Stone (but not Pitchfork, who couldn’t be bothered to review her music when she was alive). Is it wrong to think that if she’d gotten this much attention when she was alive she could have been as big as Taylor Swift? I don’t think so.
Music & Concerts
Tom Goss returns with ‘Bear Friends Furever Tour’
Out singer/songwriter to perform at Red Bear Brewing Co.

Singer Tom Goss will bring his “Bear Friends Furever Tour” to D.C. on Sunday, June 8 at 8 p.m. at Red Bear Brewing Co.
Among the songs he will perform will be “Bear Soup,” the fourth installment in his beloved bear song anthology series. Following fan favorites like “Bears,” “Round in All the Right Places,” and “Nerdy Bear,” this high-energy, bass-thumping banger celebrates body positivity, joyful indulgence, and the vibrant spirit of the bear subculture.
For more details, visit Tom Goss’s website.

Aussie pop icon Kylie Minogue brings her acclaimed “Tension” world tour to D.C. next Tuesday at 7:30 p.m. at the Capital One Arena. Tickets are still available at Ticketmaster.
The show features songs spanning her long career, from 1987 debut single, “The Loco-Motion,” to “Padam, Padam” from her album, “Tension.”