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Who discovered Taylor Swift? Who signed the pop star’s first first record deal?

With the songwriter currently at the height of her powers, we take a look back at where it all started for young Taylor.

With the songwriter currently at the height of her powers, we take a look back at where it all started for young Taylor.
| Getty Images
Joe Brennan
Born in Leeds, Joe finished his Spanish degree in 2018 before becoming an English teacher to football (soccer) players and managers, as well as collaborating with various football media outlets in English and Spanish. He joined AS in 2022 and covers both the men’s and women’s game across Europe and beyond.
Update:

Taylor Swift is currently touring the world, dating a Super Bowl tight end, raking in millions of dollars by selling millions of records and wiggling her way into the ears of just about every living organism on planet earth sufficiently evolved to be blessed with the gift of hearing.

But where did it all begin? We take a look at who discovered the talent that is currently stomping her heels all across the globe and looking more powerful than ever.

Who discovered Taylor Swift? Who signed the pop star’s first first record deal?
Toby Keith passed away in February 2024.Robert Galbraith

If you recognise the face above, it’s because you’ve probably seen Toby Keith, the man who gave Taylor Swift a pathway to her first deal, in the news recently. The country singer sadly died just a few days ago at the young age of 62. As well as his successful career as a music artist, Keith could also claim to have given Swift her first step in the industry. But we’ll get to that.

Swift’s talent was discovered when she was just a teenager back in 2004, singing at the Bluebird Cafe in Nashville. She was first ‘found’ by then-DreamWorks Records executive Scott Borchetta. The executive was impressed with Swift’s talent for country music, and wanted to sign her to a record label. However, he had the simple yet quite fundamental problem of not having one anymore.

When did Swift sign her first record deal?

Right around this time, Toby Keith had left Borchetta’s label, DreamWorks Records, seeing it shut down, and founded his own record label, Show Dog Nashville, from where he released his own music as well as signed other artists.

With DreamWorks gone, Borchetta left to start his own label, Big Machine Label Group, a joint venture between both him and Keith’s label, Show Dog Nashville, with the two becoming “sister companies” and Borchetta handily using Keith’s promotion staff.

Related stories

And so, Borchetta now had the infrastructure to sign Swift, which he duly did, and the songwriter joined the label as his first ‘big’ signing in 2005. A self-titled and largely self-penned debut album, Taylor Swift, was released on October 24, 2006.

Swift was tied to Big Machine Label Group all the way up to 2018, when she signed for Republic Records. Under Borchetta’s label, the singer released a total of 4 albums; she brought that number up to 10 with her second record label. Her latest project, entitled The Tortured Poets Department, is scheduled for release later this year.

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    Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
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    Los 40 USA
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    Entertainment

    Who is Jon Hamm married to? What to know about actress wife Anna Osceola

    The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

    The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
    NEIL HALL
    Update:

    One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

    The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

    Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

    Whirlwind romance

    Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

    For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

    Anna Osceola, from a large family

    Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

    Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

    Early career and acting roles

    She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

    Related stories

    She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

    Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

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    Complete your personal details to comment

    Your opinion will be published with first and last names

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      Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
      Editions
      Los 40 USA
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      Follow us on
      Hello
      Entertainment

      Who is Jon Hamm married to? What to know about actress wife Anna Osceola

      The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

      The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
      NEIL HALL
      Update:

      One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

      The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

      Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

      Whirlwind romance

      Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

      For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

      Anna Osceola, from a large family

      Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

      Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

      Early career and acting roles

      She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

      Related stories

      She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

      Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

      Tagged in:

      Comments
      Rules

      Complete your personal details to comment

      Your opinion will be published with first and last names

      We recommend these for you in Entertainment

        Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
        Editions
        Los 40 USA
        Scores
        Follow us on
        Hello
        Entertainment

        Who is Jon Hamm married to? What to know about actress wife Anna Osceola

        The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

        The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
        NEIL HALL
        Update:

        One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

        The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

        Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

        Whirlwind romance

        Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

        For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

        Anna Osceola, from a large family

        Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

        Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

        Early career and acting roles

        She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

        Related stories

        She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

        Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

        Tagged in:

        Comments
        Rules

        Complete your personal details to comment

        Your opinion will be published with first and last names

        We recommend these for you in Entertainment

          Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
          Editions
          Los 40 USA
          Scores
          Follow us on
          Hello
          Entertainment

          Who is Jon Hamm married to? What to know about actress wife Anna Osceola

          The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

          The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
          NEIL HALL
          Update:

          One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

          The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

          Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

          Whirlwind romance

          Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

          For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

          Anna Osceola, from a large family

          Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

          Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

          Early career and acting roles

          She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

          Related stories

          She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

          Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

          Tagged in:

          Comments
          Rules

          Complete your personal details to comment

          Your opinion will be published with first and last names

          We recommend these for you in Entertainment

            Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
            Editions
            Los 40 USA
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            Follow us on
            Hello
            Entertainment

            Who is Jon Hamm married to? What to know about actress wife Anna Osceola

            The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

            The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
            NEIL HALL
            Update:

            One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

            The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

            Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

            Whirlwind romance

            Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

            For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

            Anna Osceola, from a large family

            Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

            Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

            Early career and acting roles

            She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

            Related stories

            She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

            Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

            Tagged in:

            Comments
            Rules

            Complete your personal details to comment

            Your opinion will be published with first and last names

            We recommend these for you in Entertainment

              Who is Jon Hamm married to? What to know about actress wife Anna Osceola - AS USA
              Editions
              Los 40 USA
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              Follow us on
              Hello
              Entertainment

              Who is Jon Hamm married to? What to know about actress wife Anna Osceola

              The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.

              The Mad Men actpr met co-star and bride-to-be in 2015 and began dating during the pandemic. They tied the knot in Anderson Canyon, Big Sur in June 2023.
              NEIL HALL
              Update:

              One of Hollywood’s most eligible bachelors Jon Hamm married Mad Men co-star Anna Osceola in Anderson Canyon, Big Sur back in June 2023. They walked up the aisle to Nancy Sinatra’s 1967 James Bond theme song, You Only Live Twice.

              The couple got engaged in 2021 and had been dating since 2020. Hamm had previously been in a long-term relationship with Jennifer Westfeldt - their 18-year liaison was one of the longest and steadiest among Hollywood’s glitterati before it came full circle in 2015. “With great sadness, we have decided to separate, after 18 years of love and shared history,” they explained in a joint statement to People magazine in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

              Hamm and Westfeldt were more or less the same age, and according to several sources, she was almost like a mother figure to him, so it came as a surprise to some observers when he was rumoured to have started dating a woman 17 years his junior. The actor is believed to have first met Anna Osceola while they were both filming Person to Person in Season 7 of Mad Men. Anna had a cameo role as a receptionist, Clementine, in the final episode.

              Whirlwind romance

              Romance blossomed during the Coronavirus pandemic when they began dating. They were photographed walking Hamm’s dog Splash in the Los Feliz neighborhood of Los Angeles in late 2020. The couple were engaged in February 2023 and appeared together on the red carpet the following month at the 2023 Vanity Fair Oscar Party.

              For the first couple of years, Jon and Anna tried to keep their relationship private and away from the limelight so what do we know about the new bride? Anna was born on April 8, 1988 in Cambridge, Massachusetts.

              Anna Osceola, from a large family

              Her father, Fuad Phillip Alan Osceola, is fully qualified massage therapist with over 30 years of experience in his field while little is known about her mother Lisa. Curiously, the surname Osceola is of native American origin and relates to the Seminole Tribe of Florida. Anna has two elder sisters - Ariel and Alexandra and a brother Sam - who are now Jon’s new in-laws.

              Like all of her siblings, Anna went into higher education after high school, graduating with a Bachelor of Fine Arts degree in Drama from NYU Tisch School of the Arts on Broadway, New York City.

              Early career and acting roles

              She made her screen debut playing Charlie in spoof Not Another High School Show in 2007 although the pilot never aired and the follow-up series was subsequently scrapped. Minor walk-on parts followed in a number of films, series and TV movies and gradually some recurring roles. She played US soldier Abby Sherman in Rizzoli and Isles, Robin Wylie in the ABC family series Greek and Casey Logan, a fashion model who witnesses a member of the Russian mafia kill someone in USA Network drama, In Plain Sight.

              Related stories

              She made separate appearances in Law & Order, first as Jamie Spears in the season 18 episode Rape Interrupted, then was brought back in 2017, cast as Noelle Terlesky, who listens to Erik Menendez’s grim confession that he and his brother had murdered their parents.

              Anna starred as Larry alongside her new husband in the 2022 Miramax production, Confess, Fletch. It was reported that Hamm donated two thirds of his fee to help the producers stay within their budget.

              Tagged in:

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              Rules

              Complete your personal details to comment

              Your opinion will be published with first and last names