Edward Herrmann's Gilmore Girls character, Richard Gilmore, was always tough but fair, smart and confident, and set in his ways. He had his moments of being open to new things, like when he took magazine quizzes at Rory's birthday party, but for the most part, he wasn't up for much change.
From the pilot of Gilmore Girls, fans knew that Lorelai didn't see her parents for a really long time, and they struggled to find much to chat about once they were in each other's lives on a more regular basis. While Richard had a lot of money and success, he did experience too much sadness over the course of his life.
10 His Partner Sued Him
Richard worked with Floyd Stiles, Jason's father, and so it made sense for Richard and Jason to work together.
Unfortunately, things got really dramatic and complicated, and Jason actually ended up suing Richard later on. It was horrible and even affected Lorelai, as she was dating Jason at the time. This was really sad, as Richard had been so excited to get back to work, and he really wanted the business to be a success. This was no way to treat Richard, who was always fair when it came to business.
9 He Had A Terrifying Heart Attack While Teaching
It was really tough when Richard had some health problems in the first season, and in the seventh season, he had a heart attack.
This happened while he was teaching at Yale and it was a terrifying experience for him. It rocked his whole world as he had to slow down in terms of work after that, and that was never something that he wanted to do.
8 He Only Knew His Granddaughter When She Was 16 Onward
Rory could mess up her life in so many ways, but she had so much in common with her grandfather. They both loved reading, travel (and dreaming of the places they wanted to go), and talking about intellectual pursuits.
One of the saddest things about Richard is the fact that Lorelai kept Rory from him for so long. He only got to know her once she was 16, and while they were close and really loved each other, it's terrible that he missed out on so much of his grandchild's life.
7 His Mother Hated His Wife Emily
Richard and Emily had their fair share of problems and they didn't always discuss them.
In the first season episode 'The Third Lorelai', it turned out that Richard's mother, Trix, hated Emily. Since Richard loved his mom so much, it was definitely difficult for him not to have family support. Marrying into a family can be stressful and it never got any better for Emily, as Trix refused to be nice to her or even accept her as a big part of Richard's life. Richard seemed to ignore this a lot of the time, but he must have been pretty upset.
6 He Wasn't Considered Valuable At His Company Anymore
Rory didn't make sense all the time but she did love to work and study, and she had that in common with her grandfather.
Sometimes in movies or on TV shows someone yells "You can't fire me, I quit" and Richard essentially did this when he left the company he had worked at for years. Richard knew that he wasn't considered valuable anymore and he knew that if he waited around, he would probably be fired or slowly left out of the company. This was really heartbreaking and made him feel old and like no one appreciated all of the work he had put in.
5 He Hated Being Retired And Didn't Have Fun In His Free Time
Richard started to totally fall apart when he retired as he realized that he couldn't possibly loathe it more.
Richard was never someone who could have fun in his free time. Sure, he would sit down and read, and he and Emily did travel, but he couldn't reap the rewards of his long career and accept that it was okay to stop working. Instead, he drove himself and Emily nuts as he had such a miserable time walking around the house and wondering what to do with himself. He seemed to struggle with rest and relaxation and taking care of himself, and that's really sad.
4 His Mother Died And Emily Wouldn't Help With Funeral Arrangements
Richard showed his intelligence with most of his dialogue and he also had many sad storylines where he shut down emotionally.
In the fourth season episode 'The Reigning Lorelai', Trix died, and Richard, understandably, had an incredibly tough time. Emily and Richard had been fighting recently and instead of helping make the arrangements for the funeral, Emily decided that she didn't have to help. This made a sad situation even worse. While Emily had a good reason (she discovered a letter from Trix telling Richard to marry his ex Pennilyn), she could have told Richard how she felt.
3 He Thrived On Bragging Instead Of Finding Joy In His Life
Because of how rich he and Emily were, Richard was all about showing off. He didn't want to find joy in his life and instead of working on himself, he was always thinking about which friend, acquaintance, or business colleague he could phone and start bragging for hours.
This was really sad, as Richard should have been able to take a step back, look at all that he had accomplished, and be happy. He really did love Emily and he enjoyed his career, so he should have been a lot less miserable.
2 His Mother Didn't Think He Was A Success
Before Trix passed away, she couldn't help but insult her son and make him feel terrible.
The fourth season episode 'The Incredible Sinking Lorelais' found Trix visiting and insulting both Richard and Lorelai. She didn't think that they were very successful and she made that super clear. This was difficult for Richard to hear, as he really looked up to his mother and had always been pretty close to her. Of course, no one wants their parent to disapprove of them and their choices in life.
1 His Daughter Would Never See Him, Except When He Gave Her Money
The first season of Gilmore Girls is hilarious and sad, and many episodes explore Lorelai's relationship with her parents.
One of the saddest things about Richard is the fact that his only child never wanted to hang out with him. If Lorelai's parents didn't give her money for Rory's time at Chilton and then Yale, then chances are, Lorelai would never have come over every week (or at all). Lorelai and Richard had a terrible time dealing with one another and only seemed to speak when he was lending her cash. That's definitely heartbreaking and it was clear that Richard couldn't ever move past this.
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