Dating when you are a celebrity can be tough. The lack of privacy and pressure from the media can make it nearly impossible to maintain a healthy relationship. It can be even harder if you are dating out of your league. The constant stares and questions can be enough to strain even the strongest of relationships. Nevertheless, male celebrities have been dating out of their league for years. Take actor William H. Macy, who dated his bombshell of a wife for 15 years before finally marrying her in 1997. It seems like many attractive women in Hollywood are willing to date men who are talented but way less attractive than them.
Whether it’s due to their comedic ability, business success or sheer luck these celebrities have achieved the ability to consistently date and marry out of their league. Prominent producer Griffin Guess has not only produced projects with great musicians like Kanye West and Jay-Z but has also been married to Victoria Secret and Sports Illustrated model Marisa Miller since 2006. Cheers to the funny guys, the successful guys, and the downright loyal guys for snagging hot wives far out of their league. Clearly, there is hope for us all.
Shawn Corey Carter, more formally known as Jay-Z, is a major hip-hop mogul. In 2006, MTV ranked him the greatest MC of all time. Rolling Stone also ranked him the 88th greatest artist of all time. Growing up in the projects in Brooklyn, he sold drugs before selling CDs out of his car. As he rose to fame, he not only conquered the rap game but the business game as well. He took hold of the love game in 2008 when he married Beyonce. The two first were on the map together when they collaborated on the song “03 Bonnie & Clyde.” They kept a low profile while dating and did not talk much about their relationship in public. In 2006, they were ranked in Time’ magazine’s 100 Most Influential People as the most powerful couple and in 2009 Forbes ranked them as the most top-earning couple with a combined total of $162 million.
14. Jason Sudeikis
Catching his first break as a writer for Saturday Night Live in 2003, Jason Sudeikis got his start in improv comedy. He became a full-time cast member of the show in 2005 and stayed on until 2013. Since then he has starred in films like The Hangover and Horrible Bosses. He has also made appearances on television shows like 30 Rock and It’s Always Sunny in Philadelphia. In 2011 he began dating the beautiful actress Olivia Wilde. Wilde is known for her recurring role on the hit television series The O.C. as well as her role in the Fox medical drama House. She can also be seen directing music videos for bands like the Red Hot Chili Peppers. The two moved in together in 2012 and became engaged in January 2013. The couple has two children together, Otis Alexander, who was born in April 2014 and Daisy Josephine, who was born in October 2016.
13. Dax Shepard
Dax Shepard, hailing from the northern suburbs of Detroit, got his start in the world of acting when he moved to Los Angeles and joined the improv troupe, Sunday Company of The Groundlings. Members of the group included other comedians like Melissa McCarthy. He became known in 2003 for his work on the candid-camera show Punk’d, which starred Ashton Kutcher. In 2004, he hit the big screen and starred in the commercial hit movie, Without a Paddle, alongside Matthew Lillard and Seth Green. He started dating Kristen Bell, who is also from the northern suburbs of Detroit, in 2007 after the pair met at the birthday party of a mutual friend. While the two announced their engagement in January in 2010, they decided to delay their marriage until California legalized same-s*x marriage. On January 26, 2013, after the Supreme Court ruled the Defence of Marriage Act unconstitutional, Bell proposed to Shepard again on Twitter. The two were married in Beverly Hills in October of 2013.
12. Sacha Baron Cohen
Sacha Baron Cohen is widely known for the four fictional characters he plays. They are Borat Sagdiyev, Brüno Gehard, Ali G, and Admiral General Aladeen. Most of his work involves portraying his characters in documentary-style films where real people do not realize they are being placed into a comedic situation. He is also known for his role as the voice of King Julien XIII in the popular Madagascar film series from 2005-2012. He first met the gorgeous and hilarious actress Isla Fisher at a party in Sydney, Australia in 2002. The two were engaged in 2004. Shortly after, Fisher converted to Judaism. The two were married in Paris, France in March 2010 in a Jewish ceremony. The couple has three children together, Olive who was born in August 2007, Elula Lottie Miriam, who was born in August 2010, and Montgomery Moses Brian, who was born in March 2015.
11. Marc Anthony
Marco Antonio Muñiz, more popularly known as Marc Anthony, is a two-time Grammy winner and a five-time Latin-Grammy winner who has sold over 12 million albums worldwide. He began his career in New York as a vocalist for freestyle and underground house music acts. He got his first big break when his 1995 album, Todo a Su Tiempo, sold 800,000 copies and earned him the Billboard award for Hot Tropical Artist of the Year. In 2000, he married former Miss Universe Dayanara Torres in Las Vegas. The couple had two children, Cristian Marcus and Ryan Adrian. They separated in 2002, reconciled briefly, and then divorced for good in January 2004. Not long after the end of his first marriage, he married Jennifer Lopez in June 2004. The two first met when they recorded their duet, No Me Ames, together in 1999. The two divorced in June of 2014.
10. Benji Madden
In 1996, Benji Madden and his twin brother Joel started the band Good Charlotte. The band has since released six studio albums and continues to tour today. Madden has also helped to write and produce music with other artists like Hilary Duff and 5 Seconds of Summer. In May 2014, he began dating megastar actress Cameron Diaz. Diaz first rose to fame for her role in The Mask in 1994. Since then, she has starred in high profile films like There’s Something About Mary, Charlie’s Angels, Shrek, and many others. In 2014, she was named the highest-paid actress over 40 in Hollywood. Despite a seven-year age difference, the two married just 17 days after they were officially engaged. Even though Diaz had previously sworn off marriage, the two wed in a Jewish Ceremony on January 5th, 2014. They both still live together in their home in Beverly Hills.
9. Griffin Guess
Griffin Guess founded Machete, a production company, in 1998. Since then, he merged his company into Liberty Media and joined SVP of Commercial and Music Videos in 2002. In 2005, he became the executive producer and creative director for the company. Guess has produced hundreds of projects with top artists like Kanye West, Andre 3000, Jay-Z, Good Charlotte, and Matisyahu. In 2006, he left Liberty Media to form Cartel, Inc. Today he owns Cartel Management, Cartel Records, and Titans of Mavericks. He is also married to actress and supermodel Marisa Miller. The couple wed on April 15, 2006. Miller is best known for being a Victoria Secret Angel from 2000 to 2012 and as a Sports Illustrated swimsuit edition cover model. The pair has two sons, Gavin Lee born in 2012 and Grayson Lee Bazyl born in 2015.
8. Howard Stern
Since the age of five, Howard Stern wanted to be on the radio. As a child, he hosted his own make-believe radio shows from his basement. After working a few radio jobs while at Boston University, he started his career in 1985 with WXRK in New York City. His morning show entered national syndication in 1986 and remained on the radio until 2005. In 2006 he signed a contract with Sirius radio and moved his show onto their platform. In 2000, after the separation from his first wife, Alison Berns, Stern began dating model and television host Beth Otrosky. He announced on his radio show in February 2007 that the two were engaged. They married at Le Cirque restaurant in New York City in October 2008 in a ceremony officiated by Mark Consuelos. From their New York residence, the two have fostered and found homes for 75 cats as of June 2014.
7. David Cross
When David Cross was just 17 he began performing stand up comedy. He relocated to New York the day after he graduated high school in Atlanta. It was not until the 1990s when he became a regular at the famous comedy club chain, Catch a Rising Star, that his career truly began to take off. In 1999 he performed in a one-hour comedy special for HBO titled The Pride is Back. Since then, he has starred in the HBO comedy sketch series Mr. Show and the Fox/Netflix series Arrested Development. In August 2011, he became engaged to beautiful actress Amber Tamblyn after four years of dating. Tamblyn is best known for her lead role in Joan of Arcadia. She has also had roles in major films like Sisterhood of the Traveling Pants, The Ring, and 127 Hours. The couple married in 2012 and had their daughter, Marlow Alice, in February 2017.
6. François-Henri Pinault
François-Henri Pinault is a well known French billionaire businessman. He has been the CEO of Kering since 2005 and the chairman of Groupe Artémis since 2003. Pinault began his career in 1987 at Pinault Distribution, which became PPR in 1990. By 2005 he rose to chairman and CEO of PPR. He renamed PPR to Kering in 2013. He began dating actress Salma Hayek in 2006. Hayek began her career by starring in the telenovela Teresa and the film El Callejón de los Milagros in Mexico. She moved to Hollywood in 1991 and gained fame for her major roles in movies like Desperado and Wild Wild West. They have one daughter who was born in 2007. The couple briefly split for sometime in 2008 but then in 2009, they married on Valentine’s Day in Paris. Two months later, they renewed their wedding vows in front of friends and family in Venice.
5. Lee Kirk
Lee Kirk is a screenwriter, director, and actor best known for his work in movies like The Man Who Invented The Moon, Ordinary World, and The Giant Mechanical Man. In June 2009, he announced his engagement to actress Jenna Fischer. The two were married in Malibu, California on July 3, 2010. Fisher is best known for her role as Pam Beesly in the extremely popular NBC sitcom, The Office. In 2010, Kirk even made a guest appearance on the show as Clark the Lactation Specialist. He also directed his wife in the 2012 film, The Giant Mechanical Man. Fisher is also known for her roles in movies like Blades of Glory, The Promotion, Walk Hard: The Dewey Cox Story, and Hall Pass. The pair has two children together, a son named Westen Lee, who was born in September 2011, and a daughter named Harper Marie, who was born in 2014.
4. Geoffrey Arend
Born in Manhattan, Geoffrey Arend’s life was also was intended to be spent acting. After graduating from the Fiorello H. LaGuardia High School of Music and Performing Arts in 1996, he joined the cast of Daria in 1998. He placed the voice of Upchuck until the series ended in 2002. Since then he has had roles in movies like The Ringer and 500 Days of Summer. He also is well known for his role as Ethan Gross in the ABC series Body of Proof. He currently plays the role of speechwriter Matt Mahoney in the CBS drama Madam Secretary. On October 11, 2009, Arend married actress Christina Hendricks. Hendricks is best known for her role as Joan Holloway in the AMC television series Mad Men. She has been nominated six times for the Primetime Emmy Awards. The two have stated in interviews that they do not plan to have children.
3. William H. Macy
After graduating from Goddard College in 1971, William H. Macy moved to Chicago, Illinois to pursue acting and work as a bartender to make ends meet. There, he along with David Mamet and a few others founded the St. Nicholas Theater Company. After his time in Chicago, he moved to New York City where he had roles in over 50 Broadway and Off-Broadway plays. Since then he has had numerous roles in well-known movies and a lead in Showtime television series, Shameless. For 15 years he and actress Felicity Huffman dated on and over before finally marrying in September of 1997. Huffman is best known for starring in the ABC series Desperate Housewives. In 2012, the couple each received a star on the Hollywood Walk of Fame. They have two daughters, Sophia Grace, who was born in December 2000, and Georgia Grace, who was born in March 2012.
2. Vincent Kartheiser
Vincent Kartheiser started his acting career at a young age on the stage of the Children’s Theater Company in Minneapolis, Minnesota. He had roles in a few movies before getting his break out role as the lead along Patrick Stewart in the 1997 film Masterminds. In addition to the film, he co-starred in the television series Angel for a 28-episode run. From 2007- 2015, Kartheiser starred int he AMC television series Mad Man as Pete Campbell. In 2012, he began dating his Mad Men co-star Alexis Bledel. Bledel is best known for her role as Rory Gilmore from 2000-2007 on the television series Gilmore Girls, which was reprised by Netflix in 2016. She made her film debut in 2002 as the lead in Tuck Everlasting. The two announced their engagement in March 2013 and were married in California in June 2014. Bledel gave birth to their first child in the fall of 2015.
1. Ben Stiller
As the son of two veteran comedians and actors, Ben Stiller was always destined for Hollywood fame. He got his start at 15 when he had one line on the soap opera Guiding Light. Since then, he has starred in more than 50 films. He has also been extremely successful in his Hollywood dating career by marrying Christine Taylor. He met her in 1999 on the set of the never-aired show Heat Vision and Jack. She was a guest star in the pilot that never debuted. The two married in an oceanfront ceremony in 2000 in Kauai, Hawaii. They have appeared onscreen in major movies like DodgeBall: A True Underdog Story, Tropic Thunder, Zoolander, and Zoolander 2. They also appeared together in the television show Arrested Development. In 2002, Christine gave birth to their first child, Ella Olivia. The couple’s second child, Quinlin Dempsey was born in 2005.
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