10 Cultural Icons’ Letters to Themselves


What would you hope for yourself 10 or 20 years from now? What fears would you want to overcome? These are the questions ten pop culture icons pondered before writing a letter to themselves in the past, present, and future. Connecting the timeline of their lives, these famous personalities time traveled in order to relate important messages to their younger and soon-to-be selves that would make an impact — life lessons, life mistakes, and life milestones. See what advice, reassurance, and words of wisdom ten stars had to give to their other selves, below.

Donald Glover

Earlier this week, former Community star Donald Glover had a bit of an existential crisis at a Residence Inn — a place we imagine that happens a lot. The actor-rapper wrote a letter to himself on hotel stationery and Instagrammed the notes, in which he shared his hopes and fears for the future, the truth about leaving Community, and his struggle with his record label, Glassnote, about releasing his next Childish Gambino album. Glover also refers to “Bro Rape” in the letter, which was a video he released with group Derrick Comedy that helped spark his career.

Frank Ocean

When he was still known as Christopher Breaux and starting a songwriting career in Los Angeles, the seeds of Frank Ocean’s debut album Channel Orange were being planted in the artist’s mind. He references that time period in this letter to his “five-years-ago self” on Tumblr. Ocean writes about having his heart broken, seemingly referring to his first love, which was with a man — a relationship that inspired part of the album. Channel Orange sold 131,000 copies in its first week.

“your name is frank now..it’s a long story. your girlfriend is about to break up with you because of the long distance. it’s ok. & that job you’re working..well, you’re gonna have to work there for another year and some months.. & then you’re gonna get fired. you’re gonna work a couple more jobs after that too. nothing glamorous. kinkos and at&t if you really want the specifics. but you’re never gonna be homeless or starving. don’t worry you won’t fail and have to move back to new orleans either. you are gonna get your heartbroken though. twice. if it helps, the first one is gonna be worse than the second. contrary to how it feels, it won’t kill you. in fact it’s gonna help you write an album. yea, you finally finished an album. people like it man. you’re actually gonna write and record hundreds of songs. they won’t all be good and most ppl won’t think you’re talented at first, but you’re going to master your gifts. you’re going to become a lot stronger and wiser..even a little taller. be patient. i mean, you kind of have no choice. and be good to people. i don’t wanna spoil too much for you, but.. you’re on a plane right now to the east coast to work with kanye west & jay-z. it’s all working out kid. you made it.”

Gillian Anderson

We can’t picture poised actress Gillian Anderson being grossly selfish, especially considering her extensive charity work, but the X-Files star has been very frank during interviews about her self-absorbed and rebellious teenage years. She wrote her 16-year-old self a letter, urging the younger Gillian to love others more and quit being so neurotic.

“Dear Gillian,

You are completely and utterly self-obsessed. If you spent a quarter of your time thinking about others instead of how much you hate your thighs, your level of contentment and self-worth would expand exceptionally. One thing I learned way too late in the game for my own good was that you can effectively increase your self-esteem by doing estimable things. Therefore, I have signed you up to build homes for the homeless during your entire summer vacation. Your Christmas will be spent serving food at a battered-women’s shelter and Easter is designated to reading stories in the pediatric cancer ward. Four months out of 16 years dedicated to human beings other than yourself, you have gotten off easy. Oh and honey, expand your horizons; your world is bigger than your low self-esteem wants you to believe. Love yourself, think of others and be grateful. I love you, I believe in you, and I look forward to respecting you.

Me. You. Us.

P.S. Follow your dreams, not your boyfriends.”

Stephen Fry

While Stephen Fry was struggling with his homosexuality during his adolescence, he remained celibate for 16 years. In this letter to his teenage self, the English comedian expresses hope for the future — a time when he can be out and proud and feel worthy of love. “But don’t kid yourself. For millions of teenagers around Britain and everywhere else, it is still 1973,” he continues. “Taunts, beatings and punishment await gay people the world over in playgrounds and execution grounds (the distance between which is measured by nothing more than political constitutions and human will). Yes, you will grow to be a very, very, very, very lucky man who is able to express his nature out loud without fear of hatred or reprisal from any except the most deluded, demented and sad. But that is a small battle won. A whole theatre of war remains.” Fry concludes with a touching statement about youth:

“You poor dear, dear thing. Look at you weltering in your misery. The extraordinary truth is that you want to stay there. Unlike so many of the young, you do not yearn for adulthood, pubs and car keys. You want to stay where you are, in the Republic of Pubescence, where feeling has primacy and pain is beautiful. And you know what … ? I think you are right.”

Oprah Winfrey

This letter penned by the media mogul ruminates on the time that Oprah was entering the broadcasting business as a reporter for a local television station in Nashville. She became the first African-American news anchor at the company. Oprah discusses the abuse she endured as a child and her belief in God. “From where I sit now, viewing your journey, there are few regrets,” the talk show host and magazine editor reflects. “You wrote a poem about a ‘woman becoming.’ Even then you understood that success was a process and that moving with the flow of life and not against it would be your greatest achievement.”

Stephen King

The 1980s were a blur for Stephen King who went on a decade-long drug and alcohol binge to quell the pain of his anxieties. His addictions became so overwhelming, King doesn’t even remember writing his 1981 novel, Cujo. Eventually his family staged an intervention. King, who is now sober, wrote his teenage self a letter warning the budding novelist to stay away from drugs.

“Dear Me,

I’m writing to you from the year 2010, when I have reached the totally ridiculous age of sixty-two, in order to give you a piece of advice. It’s simple, really, just five words: stay away from recreational drugs. You’ve got a lot of talent, and you’re going to make lots of people happy with your stories, but — unfortunate but true — you are also a junkie waiting to happen. If you don’t heed this letter and change the future, at least ten good years of your life — from age 30 to 40 — are going to be a kind of dark eclipse where you disappoint a lot of people and fail to enjoy your own success. You will also come close to dying on several occasions. Do yourself a favor and enjoy a brighter, more productive world. Remember that, like love, resistance to temptation makes the heart grow stronger. Stay clean.

Best regards,

Stephen King”

Debbie Harry

Blondie front woman Debbie Harry was one of several celebs asked to write their 16-year-old selves for the book Dear Me, in order to support the Elton John AIDS Foundation. The singer hadn’t yet arrived in New York to start her career in 1961, but big things were on the way. It’s hard to imagine the gutsy punk icon needing to be reminded that she should “make a leap,” but Harry encourages her younger self to do just that in this letter.

“Dear Debbie, Moon, Debeel, or Deb,

Just because you have a lot of different names, and maybe feel like there’s a lot of different yous, don’t be confused. Give yourself some time and all the ideas and possibilities that these names conjure up for you will become clear to you. The pieces of the puzzle will reveal themselves and all you have to do is keep finding out what makes you feel happiest and this oftentimes will be the easiest thing for you to do. This is remarkable in itself. That the most obvious is often the best choice and can lead to something wonderful and satisfying.

In simpler words, go for it girl. ‘Nothing to fear but fear itself’ is such an old saying but if it helps you take a flying leap and if it’s the only thing that happens, you will have the lasting, lifelong satisfaction of having made a leap. That you have the courage of your convictions and the strength within yourself to do anything, will be your core and your future can be enjoyed even when things get tough. They will get tough and they will get easy and when you look back at those times, the rough ones will often be the ones you remember best.

Dreams Do Come True. Keep Dreaming,

Love, D”

Patton Oswalt

Funnyman, actor, and always astute writer Patton Oswalt had some stuff to get off his chest on the subjects of thievery, heckling, and rape jokes. In A Closed Letter to Myself, Oswalt tells a lengthy story about his early days in comedy clubs and an innocent mistake that taught him a few personal and professional lessons. He goes on to discuss the dreaded heckler and the ongoing debates about American rape culture:

“I’m a comedian. I value and love what I do. And I value and love the fact that this sort of furious debate is going on about the art form I’ve decided to spend my life pursuing. If it wasn’t, it would mean all of the joke thief defenders and heckler supporters are right, that stand-up comedy is some low, disposable form of carnival distraction, a party trick anyone can do. It’s obviously not. This debate proves it. And I don’t want to be on the side of the debate that only argues from its own limited experience. And I don’t need the sense memory of an actor, or a degree from Columbia, or a moody, desert god to tell me that. I’m a man. I get to be wrong. And I get to change.”

Oswalt goes on to explain “universality was never [his] goal as a comedian. Longevity and creativity are,” but his writing offers a new appreciation for the comedic profession — a gig that often gets easily dismissed.

Bruce Lee

He died only four years after writing this letter, but Bruce Lee’s dreams of fame and fortune came true before his untimely passing. His legacy is secure as one of the greatest Asian-American movie stars in the world.

“My Definite Chief Aim

I, Bruce Lee, will be the first highest paid Oriental super star in the United States. In return, I will give the most exciting performances and render the best of quality in the capacity of an actor. Starting 1970 I will achieve world fame and from then onward till the end of 1980 I will have in my possession $10,000,000. I will live the way I please and achieve inner harmony and happiness.

Bruce Lee

Jan. 1969″

Maya Angelou

Last year, poet-author Maya Angelou visited CBS This Morning to help kick-off a new program on the series called Note to Self. She wrote her 15-year-old self a delightful letter that offered a simple, but profound reminder about self-worth and ambition. “Find a beautiful piece of art,” Angelou advises in this video segment. “If you fall in love with Van Gogh or Matisse or John Oliver Killens, or if you fall love with the music of Coltrane, the music of Aretha Franklin, or the music of Chopin — find some beautiful art and admire it, and realize that it was created by human beings just like you, no more human, no less… Nothing human can be alien to you.”