Celebrities' First, Second, And Third Engagement Rings

Brad Pitt designed Angelina Jolie’s engagement ring, but how does it compare with Jennifer Aniston’s rock? Plus, What Tom Cruise, Prince Charles, Alec Baldwin, and others proposed with the second (or third) time around 

Brad Pitt
Say this about Brad Pitt—the man clearly enjoys his jewelry design. Long before he collaborated with Robert Procop on Angelina Jolie's diamond engagement ring, the Sexiest Fiancé Alive had a hand in creating what to slip on Jennifer Aniston's finger. Not only did Pitt work with designer Silvia Damiani on the swirling diamond ring he proposed to Aniston with in 1999, but he also reportedly designed the rock he gave to Gwyneth Paltrow two years earlier (though the two never made it down the aisle). While Aniston's ring was worth an estimated $500,000, experts value Jolie's at half that amount. Then again, the two do have a lot of mouths to feed.

Tom Cruise
For a man who bought Katie Holmes an engagement ring shortly after their first date, Tom Cruise wasn't taking any chances when it came to the proposal—he asked her at one of the most romantic spots on earth, the Eiffel Tower. The five-carat Fred Leighton oval diamond Cruise purchased is surrounded by six carats of smaller diamonds and estimated at $275,000. Fifteen years earlier, Cruise gave Nicole Kidman a more modest diamond engagement ring—perhaps because it was only months after his divorce to Mimi Rogers was final—but her second husband, Keith Urban, made up for that by proposing with a three-stone diamond ring and giving her a $120,000 "push present" after their baby was born. But there may be a new ring in the future for Kidman and Cruise: Their adopted daughter, Isabella, is reportedly engaged to her boyfriend, singer Eddie Frencher.

 Prince Charles
When your family has actual crown jewels, it makes proposing a lot simpler. But give Prince Charles credit—in 1981, when he asked 19-year-old Diana Spencer to marry him, the 32-year-old Prince of Wales actually bought a ring. In fact, the 18-carat sapphire surrounded by 14 diamonds was featured in Garrard's catalog when he purchased it for £30,000. (Today, that ring sits on the finger of his daughter-in-law, Kate Middleton.) Nearly a quarter century later, when Charles proposed to his longtime love, Camilla Parker Bowles, he wisely dipped into the family treasures. Charles presented Camilla with a Windsor heirloom—a square-cut diamond surrounded by six baguettes—that once belonged to his grandmother the Queen Mum.

Alec Baldwin
What kind of rocks did the 30 Rock star give the women he asked to marry him? Big ones. When Alec Baldwin proposed to Kim Basinger in 1993, he presented her with a 3.7-carat Tiffany diamond ring. In 2004, two years after their acrimonious divorce, Basinger auctioned it off for charity for $59,750—nearly double its presale estimate. And just days after Baldwin's engagement to yoga instructor Hilaria Thomas this month, she was spotted wearing a giant diamond with a platinum band that was estimated at $75,000. Despite the supersize stone, Alec's brother Stephen Baldwin insisted to Us Weekly that Thomas is "very humble, very sweet, very down-to-earth, and very charming. I'm glad that they're into each other. Alec's a lot calmer and a lot happier."

Charlie Sheen
When Charlie Sheen asked Denise Richards to marry him in 2002, he went with a ring that would have made Gordon Gekko proud. The former Wall Street star collaborated with jewelry designer Barry Kagasoff to create a 4.3-carat yellow-diamond ring set above rows of 100 small diamonds. (After Sheen gave his Spin City costar Heather Locklear a sneak peek at his choice, the former Mrs. Richie Sambora joked, "Oh my God! Richie's such a cheapskate!") Six years later, when the newly divorced Sheen proposed to third wife, Brooke Mueller, he stuck with yellow but moved up in size—Mueller got an 11-carat canary diamond worth an estimated $500,000. 

Ben Affleck
In 2002, Jenny From the Block became Jenny With the Rock when Ben Affleck proposed with a 6.1-carat pink Harry Winston diamond. Despite the $1.2 million present, the couple called off their engagement in 2004. Later that year, when Affleck proposed to Jennifer Garner, he went back to Harry Winston and purchased a 4.5-carat cushion-cut solitaire set in platinum. And he didn't stop there. After Garner became the mother of their two girls, Affleck gave her a diamond eternity band.

Donald Trump
"I always told him the size doesn't [matter]," Marla Maples said about the 7.5-carat emerald-cut Harry Winston diamond that Donald Trump gave her in 1991. "It's the symbolism." Nine years (and a daughter named Tiffany) later, after Maples and Trump were divorced, she put the $250,000 ring up for auction. "While it's rather tacky," Trump told People, "she's a very nice person. I hope she does well with the sale." She did—Donald's "symbol" fetched $110,000 at auction. In 2004, however, he broke the bank with a 12-carat Harry Winston diamond for his third wife, Melania Knauss. Though the towering Trump rock was estimated to cost between $1 million and $2 million, the groom was surprisingly modest about his selection: "It's just a nice ring," he said.

Nick Lachey
As with most important moments in their relationship, when Nick Lachey proposed to Jessica Simpson in February 2002, the intimate scene was captured for the cameras: While vacationing in Hawaii, Lachey asked Simpson to marry him with a pear-shaped diamond she is clearly giddy about. The second time around, Lachey stepped up his game. In November 2010, he asked Vanessa Minnillo to marry him with a four-carat Asscher-cut diamond ring surrounded by baguettes—estimated to cost $125,000—designed by New York City jeweler David Bader of Bader & Garrin. (The couple went back to Bader when it was time to make wedding bands. "Vanessa was definitely looking for a ring to match her engagement ring," Bader told People.) And not to be upstaged, a week after Lachey's engagement, Simpson had a new ring of her own—a ruby-and-diamond Neil Lane ring that former NFL quarterback Eric Johnson gave her when he proposed.

Paul McCartney
The man who wrote "Can't Buy Me Love" clearly understood it's not the size of the rock, it's how solid the relationship is. But Paul McCartney probably should have paid attention when his second wife, Heather Mills, threw her relatively modest $21,000 engagement ring at him during a prewedding argument. (She later also lost the ring on a golf course but then found it.) And though their 2008 divorce cost McCartney nearly $50 million, it didn't deter him from proposing to Nancy Shevell last May with a stunning sparkler: The former Beatle gave Shevell a vintage 1925 Cartier solitaire worth an estimated $650,000. He also reportedly refused to sign a prenup. And with a love like that, you know you should be glad.

Richard Burton
Elizabeth Taylor once famously joked, "My mother says I didn't open my eyes for eight days after I was born, but when I did, the first thing I saw was her engagement ring. I was hooked!" Which means the bar was fairly high for her eight husbands. It was No. 5, Richard Burton, who gave Taylor her most famous jewels—including the Krupp Diamond, La Peregrina Pearl, the Taylor-Burton diamond. But when he proposed in 1964, he made a bold choice: He didn't opt for a ring. Instead, Burton gave Taylor an 18.6-carat Bulgari emerald pendant necklace surrounded by diamonds. (Is it any wonder she divorced him a decade later?) When Burton got remarried in 1975—to Taylor—he outdid himself. The actor purchased the Duchess of Russia emeralds, which he had set by Bulgari as earrings, a necklace, and a bracelet. Taylor's extraordinary jewelry collection—which included those engagement gifts—broke an auction record at Christie's last December, selling for $137 million.