Bob Dylan is undoubtedly one of the most iconic singer-songwriters in American history. Over his 60+ year career, Dylan has kept notoriously private about his personal life, letting his music speak for itself.
But Dylan has also been busy on the family front, having six children who’ve grown up and started families of their own. What’s remarkable is that so many of Bob Dylan’s kids have inherited his musical talents and passions, continuing his legacy across multiple generations.
Let’s take a deep dive into the musical gifts and careers of Bob Dylan’s children.
Bob Dylan’s Marriages and Growing Family
In the 1960s, a young Bob Dylan was married to a model named Sara Lownds. Sara inspired many of Bob’s love songs during that era like “Sad Eyed Lady of the Lowlands.” Together they had four children – Jesse, Anna, Samuel, and Jakob Dylan, who arrived in quick succession between 1966 and 1969.
After 12 years of marriage, Bob and Sara ultimately divorced in 1977 as Bob’s music career boomed.
Little did the public know, but in 1986 Bob Dylan secretly got married again, this time to one of his backup singers, Carolyn Dennis. They had a daughter together named Desiree in 1986.
Bob managed to keep the marriage completely out of the spotlight until 2001 when the news of his second wife and child finally emerged in a biography about him. True to his private form, Bob and Carolyn Dennis had quietly divorced back in 1992.
So in total, the legendary singer-songwriter had six children between his two marriages: Jesse, Anna, Samuel, Jakob, and Desiree.
Plus, an adopted daughter named Maria from Sara’s previous relationship before Bob entered the picture. For someone so laser-focused on his music, Bob Dylan had a pretty large family going on behind the scenes!
Jakob Dylan Finds Success with The Wallflowers
Jakob Dylan grew up surrounded by his dad’s musical gifts. As Bob Dylan’s youngest son, Jakob started his own band in 1989 called The Wallflowers alongside childhood friends.
Their 1992 debut album had modest success, but it was 1996’s “Bringing Down the Horse” that propelled The Wallflowers and Jakob to stardom.
The hit single “One Headlight” won the Grammy for Best Rock Song in 1998. Jakob had clearly inherited his father’s songwriting talents, creating his own legacy.
The Wallflowers continued releasing albums throughout the 2000s, with Jakob Dylan leading the way as the band’s singer-songwriter. While his raspy vocals sound similar to his dad’s, Jakob’s goal wasn’t to copy Bob Dylan’s folk style.
The Wallflowers carved out a niche in more mainstream, radio-friendly rock than Bob’s traditional folk roots. Impressively, Jakob seemed determined to succeed based on his own merits rather than simply leverage the Dylan family name.
Of all Bob’s children, Jakob has come the closest to emerging from his father’s shadow.
Jesse Dylan’s Hollywood Career
In contrast to his musical family members, Bob Dylan’s eldest son Jesse found his creative talents behind the camera. Jesse carved out a successful career directing films and television shows, providing a visual outlet versus a musical one.
In the 1990s, Jesse directed several comedy films like How High and Kicking and Screaming. He also founded the production company Wondros, further establishing himself in Hollywood.
In recent years, Jesse has directed episodes for hit shows like Sons of Anarchy and The Talk. He also executive produced the TV movie Brothers and the sitcom Conspiracy Theory. Most recently, Jesse got to direct his iconic father in a 2022 music video for the singer Cher.
It seems Bob passed down his creative genes to Jesse, just in a different format. While Jesse’s career hasn’t focused on music, he’s undoubtedly made his famous father proud.
The Elusive Anna Dylan
Unlike her two brothers embracing the arts, Bob Dylan’s middle child Anna has shunned the spotlight entirely.
After growing up in the glare of fame and press surrounding her father, Anna opted for a very private life outside of Hollywood or the music business. There are rumors she works as an artist, but few details are known about her career and interests.
Of all his children, Anna seems to represent Bob Dylan’s own protective and private side. Growing up with a globally worshipped musician for a dad couldn’t have been easy. She valued living a normal childhood away from cameras and reporters.
Now as an adult, Anna maintains the privacy and separation from fame that her reclusive father modeled. She remains a bit of a mystery among Bob Dylan’s kids.
Samuel Dylan’s Quiet Life
Bob and Sara Dylan’s third child, Samuel, grew up to live a relatively quiet life in Minnesota with his wife and kids. Professionally, Samuel worked anonymously as a photographer for many years.
Recently, reports have circulated that Samuel operates a metal fabrication business. Like his sister Anna, Samuel values his privacy highly and has avoided any media coverage about his personal or work life.
Of all his children, Samuel seems to share the most in common with his introspective, artistic father. He represents another side of Bob’s personality that eschews fame in favor of more solitary, humble work.
One imagines Bob and Samuel connecting about their mutual love of observing life quietly through a camera lens and finding insight. While we don’t know much about Samuel, he seems to have followed his passions out of the public eye.
Maria Dylan: Lawyer and Mother
Bob Dylan’s first child arrived through adoption. When Bob married his first wife Sara Lownds in 1965, he officially adopted her young daughter Maria from a previous relationship.
As the oldest of Bob’s children, Maria has said she struggled with feelings of loneliness and being overshadowed by her intensely famous father while growing up.
Rather than pursue music or entertainment like her younger siblings, Maria forged her own path in law. Today she practices as a lawyer in Santa Monica, California and is a mother of four children herself.
Out of Bob’s kids, Maria has been the most forthcoming in interviews, speaking candidly about both the joys and difficulties of being Bob Dylan’s daughter. She yearned to establish her own legacy distinct from her father’s.
The Next Generation of Dylan Musicians
Bob Dylan’s musical gifts have continued blossoming through his grandchildren as well. Jakob Dylan’s sons have begun playing in an informal family band called Winston Dylan, occasionally joined by their talented grandfather.
Bob Dylan’s grandson Pablo is growing up surrounded by instruments in Jakob’s San Francisco home studio. Meanwhile in Los Angeles, Jesse Dylan’s two sons both play music just for fun in their free time.
It seems a passion for melodies, lyrics, and instruments runs deep throughout the Dylan family tree. Even as teenagers, Bob’s grandkids are already showing musical inclinations, whether jamming at family gatherings or taking after their fathers at band practice.
They represent the next generation now benefitting from their grandfather’s wisdom and artistic legacy. Bob may have tried keeping his personal life private, but his music left a lasting impact on his children and even his grandchildren.
Final Thoughts
The idea of the family often gets sidelined when discussing notoriously solitary icons like Bob Dylan. However, the musical gifts embodied by his children reveal so much more about his lasting influence.
Both Jakob and Jesse carried on their father’s creative spirit through songwriting and filmmaking respectively.
Meanwhile, Anna, Samuel, and Maria chose lives away from the spotlight, mirroring their father’s own introverted nature. Even Bob’s grandchildren are continuing the musical lineage.
There are now over 50 years of Dylan talent being passed between generations – and it doesn’t seem to be stopping anytime soon!
About the Author
Team Guitar Top Review Talk about Guitars! We are a group of friends that bonded over their shared love of playing guitar. We all have different backgrounds and experiences with music, but we share a passion for writing about the things that we love.