My Tireless Investigation Into the Winston Churchill Sample on Hilary Duff’s 2007 Magnum Opus

Dignity is a neat collection of electro-pop bops—a departure from Duff’s earlier pop-rock-leaning records—that doubles as both an (occasionally) biting commentary on the pervasive celebrity culture of ’00s-era young Hollywood, and also as the singer’s Most Personal Album To Date, a crucial step in the trajectory of any ex-Disney, all-growed-up pop star worth her salt. Duff had writing credits on nearly every track, and the media declared that the majority of the album was a dig at Richie, a reigning LA It Girl at the time.

“You’d show up to the opening of an envelope. Why does anybody care about where you go?” Duff sneers on the album’s title track, which decries the shallowness of fame. “Where’s your dignity? I think you lost it in the Hollywood Hills.” On the Churchill-sampling “Gypsy Woman,” she sings of a malevolent man-eating woman who “lets you think that you found her first. That’s how she works, her sick and twisted gypsy curse.” Duff then warns the woman: “Enjoy the fame, bringing down the family name,” a lyric that Reuters suggested referred to Richie, Lionel Richie’s daughter, who was, at the time, considered to epitomize the idea of being famous for being famous. Entertainment Weekly suspected these songs were inspired by Madden “speedily rebound[ing] into the twiglike arms” of Richie, while Access Hollywood accused the singer of taking “pot shots” at the new couple.

Duff was eventually forced to address the matter publicly, telling Reuters she has no issue with Richie. “I broke up with my boyfriend, and I expect him to date other people, and I don’t know her, and I don’t have a problem with her,” she said. She also claimed that “Gypsy Woman” wasn’t about Richie at all and was instead about a woman who had an affair with her father, Robert Duff, which ended her parents’ marriage. “I was embarrassed that my family wasn’t perfect and that some woman had broken it up,” she told Star magazine at the time. “It’s much more meaningful than what Nicole Richie means to me,” she said of the song (which was co-written with her older sister, Haylie) to Reuters. 

With Richie and Madden now out of the picture, I wondered if the Churchill sampling was some sort of allegory for the cold war raging between Robert and Susan Duff over his misdeeds with an “attractive” (to quote Star) flight attendant—with Hilary and Haylie taking an allied stance on their mother’s side.

While I had a clearer picture of the song’s genesis, I realized that if I wanted real answers, I’d have to go straight to the source.

In addition to Haylie, Duff wrote “Gypsy Woman” with OneRepublic frontman Ryan Tedder, who also produced the track. Tedder, regarded today as one of pop’s most reliable hitmakers, seemed like a good place to start. Though the pop Svengali would later go on to pen such mammoth hits as Leona Lewis’ “Bleeding Love,” Beyoncé’s “Halo,” and Ellie Goulding’s “Burn,” in 2006 Tedder was just a fledgling songwriter with a handful of credits under his belt on the Step Up soundtrack and for acts like Russian pop duo t.A.T.u. Could the Churchill sample be the fruit of an ambitious new producer, keen to leave his mark on the music industry?

Sadly, Tedder, via his publicist, declined to comment on the matter.

Next, I turned my attention to the Duff camp. Could Duff have surreptitiously included the Churchill sample as an Easter egg for fans with a keen ear for both pop music and 20th-century history? Maybe Duff was, in fact, waiting for someone to notice this peculiar artistic choice and finally give her the opportunity to explain its meaning.

However, her representatives also declined to comment.

But I remained steadfast in my quest for the truth—after all, there was still Haylie (the same words I expect are almost always uttered before someone reaches out to a representative for Haylie Duff).

The Ashlee to Hilary’s Jessica, Haylie is probably best remembered for co-starring in Material Girls with her famous little sister and for a brief legal spat with Paris Hilton over the rights to a song called “Screwed,” a cool slice of ‘00s pop-rock perfection that eventually landed on Hilton’s self-titled debut album. Save for a couple of guest episode spots and a short-lived cable cooking series, it didn’t seem like the older Duff sister had been too busy, professionally speaking, in recent years. I hoped this would mean she’d be more open to speaking with me. She was not; her representatives also declined.

I realized I needed to cast a further net and soon found myself reaching out to a musician named Alain Johannes, who’s credited with mixing the track. Interestingly, a representative for Johannes responded to say that, despite what the album credits state, he did not do any mixing on the album. “He did play a couple of guitar solos, but otherwise had very little to do with the record,” Johannes’ rep said. “Sorry…” Sorry indeed, sir.

Finally, I turned my attention to Churchill himself. Surely, I thought, the voice and words of such a prestigious figure are protected in some way and, if so, what might have persuaded that governing body to agree to this posthumous collaboration? Save for the possibility of the descendants of Churchill being avid Lizzie McGuire fans, it’s hard to imagine how they’d have justified approving this. Unless, they were persuaded by money changing hands—if so, what’s the premium on using a war hero’s voice to introduce the fifth track of an ex-Disney star and gay rights activist’s third album? 

The literary works of Sir Winston Churchill, including his speeches, do indeed remain in copyright, according to Curtis Brown, the agency that represents former prime minister’s literary estate. Per the agency’s website, in order to use a quote from Churchill’s speeches, written or audio, you must apply for permission through the agency. Logically, I assumed someone there might recall the fateful day when Duff and Tedder’s request came in to clear the sample. But, an assistant for Gordon Wise, the agent who looks after the Churchill Estate (and the Literary Agent of the Year 2015, no less), confirmed to me via email that he knew nothing of “the specifics of this.” However, he also noted that the permissions granted by their clients are confidential.

Undeterred, I sought to get closer to the source and cut out the middleman; after all, an agent is only administrating on behalf of their client. So I reached out to the International Churchill Society, the organization dedicated to preserving Churchill’s legacy and literary estate. Justin Reash, the executive director, was unable to shed any light on the matter—on account of the fact that the Society no longer employs anybody who worked there in 2006. 

I’ll admit, at this point, I was beginning to become suspicious of this wall of silence I was facing from all sides. Could it really be that the answers I sought had been lost to the ravages of time? Or was there a more sinister reason why all parties involved in this bizarre meeting of minds remained so tight-lipped?

Having more or less run out of road, I was about to call it quits when another key figure entered the frame: Andre Recke, Duff’s one-time manager and A&R guy, who’s also listed as an executive producer of Dignity. After multiple e-mails from yours truly, Recke finally responded…only to tell me to reach out to the writers and producers of the album (way ahead of you, buddy).

Had I inadvertently pulled the curtain on the ugly truth that Duff had, in fact, besmirched the name of Sir Winston Churchill by using his voice without permission on a song about the woman who (allegedly) broke up her parents’ marriage?

However, he also offered that “based on this being Sir Winston Churchill’s most famous speech which was publicly broadcasted in 1940, the copyright for public broadcasts expire after 50 years and become public domain.” If this were true, it would explain why nobody in the Churchill camp knew (or really cared) about the sample. But it also directly contradicts the very existence of the permissions process they said must be followed to reproduce Churchill’s work for commercial use. As dogged a reporter as I am when it comes to the Hilary Duff beat, I’m no expert on copyright law and so, I thought it best to corroborate Recke’s explanation with an attorney.

John Wood, founding attorney at Grant Park Legal Advisors, which specializes in copyright and business law, immediately cleared this up. “The materials produced in 1940 would still remain under copyright in 2007,” Wood said. “They remain under copyright now.”

As it turns out, there are actually a number of different copyrights at play here (stay with me now). First, there’s the copyright of the speech itself, owned by Churchill’s estate and administered by Curtis Brown. Then there’s the copyright of the sound recording, owned by Decca Records (part of Universal Music, a rep for which also declined to comment on this matter). Finally, there is the copyright of the broadcast, as the speech went out on airwaves across the U.K., which sits with the BBC.

hilary duff – gypsy woman | dignity tour | 2007 pic.twitter.com/4cr7kqQJVk

— Hilary Duff Updates (@HilaryUpdatez) April 14, 2023

“The speech itself is protected until 70 years after his death (2035),” Wood added. “The sound recording, assuming it was made in 1940, would also enjoy protection for 70 years because it was played/ broadcast to the public (2010). The broadcast copyright would have expired in 1990.” While we can’t be sure if the sound of Churchill’s voice in “Gypsy Woman” comes from a sound recording or the broadcast, whatever way you cut it, there’s at least one copyright at play here that would have required a license. “Hilary Duff (or her record label) probably needed two types of permissions that she did not ask for,” Wood concluded. The attorney also added that Duff and co. “might have run into issues with how the material was being used,” which I am inclined to agree is a reasonable assumption here given the nature of the usage—I struggle to believe the Churchill estate was concerned with having a stake in the 2007 Young Hollywood scene.

Newly enlightened on the nuances of copyright law, I wondered if my earlier suspicion of collusion between the Duff and Churchill camps was way off the mark. Had I inadvertently pulled the curtain on the ugly truth that Duff had, in fact, besmirched the name of Sir Winston Churchill by using his voice without permission on a song about the woman who (allegedly) broke up her parents’ marriage? A song, it must also be noted, that carries some rather unfortunate derogatory connotations for the Romani community? (However, there is ample evidence to suggest Churchill likely would not have had any second thoughts about offending the Roma people.) Was Duff’s want for vengeance on this fabled woman so all-encompassing that she would disrespect one of history’s most respected leaders?

In an article posted on the International Churchill Society’s website, author and historian Dr. Stephen Bungay explores what exactly it was about the late prime minister’s way with words that made him the great orator he’s remembered as. “Churchill was a master of what we now call the sound bite,” Dr. Bungay writes. He suggests that phrases such as “this was their finest hour” and “never was so much owed by so many to so few,” have become so emblematic, even borderline cliché, that they’ve taken on a life of their own beyond the speeches in which they were first uttered. Clearly Dr. Bungay has at least one supporter of his hypothesis in Hilary Duff. After all, it’s because of her that “the Battle of France is over” now sits chiefly among these iconic Churchill quotes, having truly achieved a life and legacy of its own, far beyond what Churchill could have ever imagined when he addressed the House of Commons in 1940.

In the absence of confirmation from Duff herself, I’m left to draw my own conclusions. And in the spirit of kindness, I’m going to take it for granted that she, an undeniably worldly woman, was indeed aware of who Churchill was, and she still is now. Nonetheless, I’m not ruling out the possibility that she was unaware that the voice of the man in her song belonged to Churchill. As to why OneRepublic’s Ryan Tedder would select this clip out of all available sounds, my mind truly cannot compute.

I’ve come to accept that we may never know exactly what took place in the studio the day “Gypsy Woman” was conceived. But perhaps great art needs no explanation. Maybe Duff wanted to leave the work open to the listener’s interpretation, to let the music speak for itself. 

“Out of all the thieves that trained her, none of them could tame her,” Duff sings. It struck me, in hearing the song for what was conservatively the 102nd time, that there’s a certain reverence in the way she describes the woman here, as though Duff, on some level, almost admires her primal need to run wild. Maybe that’s enough. Maybe we’re all just waiting for someone to tell us we’re free of the battle we’ve been fighting. Maybe we’re simply born to roam free, shameless, and unbridled, like a gypsy—or at the very least, like an attractive flight attendant.