Who Got the Better Ring?

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 the Eiffel Tower, and the estimated $275,000 five-carat Fred Leighton oval diamond is surrounded by six carats of smaller diamonds. Fifteen years earlier, Cruise gave Nicole Kidman a more modest engagement ring, but Kidman's second husband, Keith Urban, made up for that by proposing with a $120,000 "push present."

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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. And just days after Baldwin's engagement to yoga instructor Hilaria Thomas last month, she was spotted wearing a giant diamond with a platinum band that was estimated at $75,000.

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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 later, after Maples and Trump were divorced, she put the $250,000 ring up for auction. In 2004, however, he broke the bank with a 12-carat Harry Winston diamond for his third wife, Melania Knauss, estimated to cost between $1 million and $2 million.

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Prince Charles

In 1981, when Prince Charles asked a 19-year-old Diana Spencer to marry him, the 32-year-old Prince of Wales actually bought a ring. 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 25 years later, when Charles proposed to Camilla Parker Bowles, he instead dipped into the family treasures for her Windsor heirloom square-cut diamond surrounded by six baguettes.

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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 was 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.

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.

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 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. Six years later, when the newly divorced Sheen proposed to his third wife, Brooke Mueller, he stuck with yellow but graduated in size—Mueller's 11-carat canary diamond is worth an estimated $500,000.