You’re digging through an old jacket or maybe you just sold something on Craigslist, and there it is. A crisp, slightly older-looking Benjamin. You notice the date: Series 1999. Suddenly, your brain goes to that place we all go—is this one of the rare ones? Is a 1999 100 dollar bill worth more than face value, or is it just a hundred bucks that’s been sitting in a drawer for twenty-five years?
Honestly, the answer is usually boring. But sometimes, it’s not.
Most people see a "Series 1999" note and assume it's part of the old-school small-head era, but it’s actually right in the middle of the transition. These are the "New Currency Design" notes. They have the large, off-center portrait of Benjamin Franklin that we saw throughout the late nineties and early 2000s, before the "colorized" peach-and-blue notes took over in 2013.
If you have one in your hand, you’re holding a piece of history from a time when the Treasury was frantically trying to outrun North Korean counterfeiters.
What’s Actually Happening with 1999 100 dollar bill Values?
Let’s get the reality check out of the way first. If your bill is wrinkled, has a "Happy Birthday" written in ink on the corner, or looks like it’s been through a washing machine, it’s worth exactly $100. Banks see these every single day. They aren't rare in the sense of a 19th-century gold certificate.
But collectors—the folks who actually spend their weekends on Heritage Auctions or lurking in CoinTalk forums—look for very specific things.
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A 1999 100 dollar bill in "Gem Uncirculated" condition, meaning it looks like it was printed five minutes ago with zero creases, can fetch anywhere from $120 to $150. That might not sound like a jackpot, but it’s a 50% profit just for keeping a piece of paper clean. The real money enters the room when we talk about Star Notes and serial numbers.
The Star Note Mystery
Look at the serial number. Is there a little star at the end instead of a letter? If yes, you’ve got a replacement note. When the Bureau of Engraving and Printing (BEP) screws up a sheet of bills, they can’t just print the same serial number again—that would mess up the accounting. Instead, they swap in a "Star Note."
For the 1999 series, some Star Notes are common. Others are scarce. It all comes down to the "run size." If the BEP only printed a small run of 640,000 star notes for a specific Federal Reserve Bank—let's say the Richmond (E) or Kansas City (J) banks—collectors go nuts. A high-grade 1999 100 dollar bill with a star from a rare run can easily clear $300 or more.
Why 1999 Was a Weird Year for Benjamins
The late nineties were a chaotic time for American money. We were just coming off the 1996 redesign, which was the first major change to the $100 bill's look since 1928. People were suspicious. There were rumors that the new large-head bills wouldn't be accepted overseas or that they had tracking chips in them (they didn't).
By 1999, the BEP was cranking these out at two main facilities: Washington D.C. and Fort Worth, Texas.
You can tell if yours is a Texas native by looking for a tiny "FW" in the corner. Does it make it worth more? Usually no, unless you find a collector trying to complete a "district set" who happens to be missing that specific combination of year, factory, and Federal Reserve branch.
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Security Features You Should Check Right Now
If you're worried about whether your 1999 100 dollar bill is even real, you don't need a fancy UV light, though it helps. Hold it up to the sun.
- The Watermark: You should see a ghost-like image of Ben Franklin on the right side. It should look like the portrait, not a cartoon.
- The Security Thread: There is a thin vertical strip that says "USA 100." In a 1999 note, this glows pink under a blacklight.
- Color-Shifting Ink: Look at the "100" in the bottom right corner. Tilt the bill. It should change from green to black. If it stays green, you don’t have a rare bill; you have a fake bill.
The "Fancy" Serial Number Rabbit Hole
This is where the 1999 series gets fun. Since these bills are older, many of the "cool" serial numbers have already been pulled out of circulation or lost. If you find one now, you’ve beaten the odds.
What constitutes "fancy"?
- Ladders: 12345678 or 87654321. These are the holy grail.
- Radars: Numbers that read the same forward and backward, like 44999944.
- Solid Strings: If the serial number is all 7s or all 3s.
- Low Numbers: Anything below 00001000.
A 1999 100 dollar bill with a serial number like AL00000001 would be worth thousands. Seriously. People collect these like Pokemon cards.
Misprints and Errors: The Real Jackpots
Errors happen. Not often, but they happen. In the 1999 run, you might find "Gutter Folds," where the paper was folded before the ink hit it, leaving a white streak through the design. Or "Inverted Overprints," where the seals and serial numbers are upside down.
These aren't just "neat." They are valuable. An authenticated 1999 error note can sell for $500 to $2,000 depending on how dramatic the mistake is. If the green Federal Reserve seal is printed over Ben’s face, stop touching it and put it in a plastic sleeve immediately.
Modern Spending vs. Collecting
Can you spend a 1999 100 dollar bill at Starbucks? Yeah, sure. But you might get a weird look from a nineteen-year-old cashier who wasn't born when that bill was printed. They might even think it's fake because it lacks the "3D Security Ribbon" (the blue strip) found on the 2013 notes.
That’s actually a good thing for you.
The more these bills get pulled from circulation and destroyed by the Fed because they are "soiled" or "worn," the rarer the surviving 1999 notes become. We are currently in a window where they are common enough to find but old enough that people are starting to save them.
How to Handle Your Bill
If you think you have something special, do not clean it.
I can't stress this enough. Don't iron it. Don't use soap. Don't try to "brighten" it. In the world of paper money collecting, "cleaning" a bill is the fastest way to kill its value. Collectors want original paper waves and crispness. If you wash it, you remove the natural oils and the "embossing" (the raised feel of the ink), and the value drops to face value instantly.
Instead, go to a local coin shop. Ask them for a PVC-free currency sleeve. It’ll cost you about fifty cents.
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Actionable Steps for Your 1999 Series Note
If you’re staring at a 1999 100 dollar bill right now, here is exactly what you should do to determine if it’s worth more than a hundred bucks:
First, check the corners. Are they sharp? If the bill is floppy like a piece of cloth, it’s a "circulated" note. Unless it has a crazy serial number or a star, it’s just a spender.
Second, look at the serial number. Check for patterns. Use a site like "My Currency Collection" to plug in your serial number and see if it’s a rare Star Note run. They have a lookup tool that’s basically the industry standard for this.
Third, look for "The Big Three" errors. Check for ink smears, misaligned borders (where the design is shifted way to one side), and "doubled" printing.
Fourth, get an appraisal if it’s weird. If you genuinely think you have a rare error or a perfect-grade bill, don't sell it on eBay yet. Look up "PCGS Banknote" or "PMG Grading." These are the companies that "slab" money in plastic and give it a numeric grade from 1 to 70. A 1999 note graded "66" or higher is where the real price appreciation lives.
Finally, decide on your "Hold" strategy. If the bill is just "okay" but you like it, keep it. Inflation might be eating the purchasing power of that $100, but the numismatic value of 1990s-era currency is slowly climbing as the "Large Head, No Color" era fades into history.
Don't let a cashier tell you it's fake just because it looks different. Know your security features, know your serial numbers, and keep your eyes peeled for those stars.
You'd be surprised how many people spend a $500 rarity on a bag of groceries because they didn't take ten seconds to look at the serial number.