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Large-denomination bills were never formally taken out of circulation, but the last ones were printed in 1945 and the Federal Reserve stopped sending them to banks in 1969. By now any that were left have been grabbed by collectors. The largest bill still printed is $100.

In fact the Treasury has never withdrawn or demonetized any currency except for gold certificates, so even 1928 $1 bills are still legal tender. But the chances of finding anything like that in circulation are effectively zero.

In any case, it wouldn't make sense to try to spend one - aside from the questions it would raise, they're possibly worth much more to a collector. The most common ones (1934-A Federal Reserve Notes) sell for a couple of hundred above face value even when worn, and other series can be worth upwards of $15,000.

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