Wheelbarrow
Introduced in the 1950s, the 'barrow was brought on board to symbolize hard work across farmland, and we guess for kids transporting tools in their sandbox. Well that failed. The wheelbarrow NEVER rests in place; it slumps over too often which, in turn, symbolizes total plow breakdown and negligence. We can't imagine under what circumstance a person would want to be Wheelbarrow.
Boot
Boot's been around since Day One. Representing hard work—it's based on a leather work shoe, and we’re down with sturdy boots—Boot is a fine choice thanks to its handy shoe horn and steady footing, pun intended. If it were life-size, a player could drop his cash and coins inside with no worry of losing any of his loot. Also if it were life-size and steel, one could probably drink out of it.
Top Hat
This is where we’re at here. This is how We see ourselves like 44% of the time and we bet you do, too. And why wouldn't you? Everyone likes hats, and everyone loves fancy hats. Stop fighting it. As you know, Top Hat is among the original pieces, and sits atop the head of Mr. MONOPOLY. Call us crazy, but Top Hat's popular for a reason and demands respect.
Race Car
According to a 1998 poll, the racecar is the most used MONOPOLY piece. We can see that, and we doubt much has changed in 24 years. What's more appealing to a kid (or adult) than a mid-20th Century-era Indy 500 car made popular by Wilbur Shaw? The piece itself never loses balance zooming around the board—plus, old-timey cars inherently exude wealth on their own, so it's like starting the game with an extra $100. Even though it isn't. But still.
Thimble
You, if you're like us, played MONOPOLY for the first time when you were a kid. You had smaller hands then, and hence, smaller fingers. Was there a better feeling than sticking your pinky in there and instantly growing a claw? No, there was not. Even now, with your grown-up hands, Thimble just feels right and never falls over. It slides smooth, and doesn't take up a lot of room. Oh, Thimble, always so considerate of others.