What Does Jack the Lad Mean?

Jack the Lad Meaning

Definition: A confident and carefree man who enjoys having a good time.

Origin of Jack the Lad

This expression originated in the 1800s. It is unclear if it comes from a real person named Jack, but some sources speculate it comes from Jack Shepherd.

He was a thief from the 1700s who had a reputation for being confident, wild, and exciting.

Examples of Jack the Lad

what is a jack the ladIn the conversation below, two friends are discussing a break up that one of them just went through.

Scott: I’m glad to see you getting out more. Are you feeling any better after breaking up with Lindsay?

Tony: Not really. She’s already starting to date someone new.

Scott: Well, good. She’s moved on, and so should you.

Tony: He just seems like a horrible person. He’s a real Jack-the-lad type. She needs someone serious, hardworking, and dedicated to be her boyfriend. He’s not like that at all. He’s only interested in having a good time.

Scott: Well, maybe you should focus on yourself more and less on Lindsay. Maybe she just wants to have a fun relationship that isn’t so serious.

jack the lad musicTwo coworkers use the expression while talking about their children.

Richard: Miranda, can I ask you something?

Miranda: Sure. Go ahead.

Richard: How do you get your son to get such good grades? My son works so hard, but still is almost failing most of his classes.

Miranda: Well, I wish I could help you, but unfortunately I don’t have any advice. My son is a bit of a Jack the lad. He never studies and doesn’t worry about his grades at all. However, he always aces his tests without any effort. He’s sort of unusual in that way.

Richard: Lucky him! I wish my son had that same situation.

More Examples

The first example uses the expression to describe an actor who was right for a role.

  • “Phil’s a natural. He’s got a raw talent, and he’s brimming of confidence. He’s Jack the Lad, and that’s what we wanted,” says Green, 35, bearded and enthusiastic. –LA Times

The second example is from a book review.

  • Stewart’s antics have earned him a richly deserved Jack the Lad reputation. But that doesn’t mean they’re rich enough to support a good book. It’s his storytelling style, which mixes wild boastfulness with barely credible self-deprecation, that proves so winning, if only because he is so willing to embarrass himself. –New York Times


The term jack the lad is a name people call a man who doesn’t have worries and does whatever he wants, regardless of the consequences.

Usually this man is also successful in his endeavors.