Racing the Train

"... the tie goes to the train."

—Old railfan saying

He saw
The train
And tried to duck it
Kicked first the gas
And then the bucket

—Burma-Shave

So, you've got a speedster... let's call him Steve. There are many ways you can show off a character's powers—guys with Super Strength can lift buses, gals with Flight can jump off tall buildings and not plummet to their deaths, guys with Heart can... uh... that's not important. But what can good ol' Steve Speedster do? Race a bullet train, that's what!

Basically, someone shows off how fast they (or their Pimped-Out Car) are by running parallel to, or if he's particularly cocky, in front of a train. It goes without saying that this is a horrible, terrible, no-good, very bad idea in Real Life.

Examples of Racing the Train include:

Anime and Manga

In one of the Choujin Olympics in Kinnikuman, Terryman had to race ahead of a train he himself had pushed as part of a qualifier round because a puppy had wandered onto the track. Saving the puppy meant stopping the train which, despite his heroism, got Terryman disqualified.

Comic Books

In one issue of The Flash, Wally realizes that while he was fighting a supercriminal, his girlfriend was taking a train and leaving town. He then proceeds to run down the train, climb on board, and asks her to stay.

Film

Occurs in the original The Fast and the Furious. They both make it.
Stand by Me has the boys racing a train on foot.
A young Clark Kent does this in the movie Superman.
A Chase Scene between Trey and Ford in Torque ends on this note.
A version of this happens in Legend of Zorro when the horse, Tornado, is racing to catch up to the train
The famous Chase Scene in The French Connection.
Cars: Lightning McQueen does it while trying to catch up to what he thinks is Mac, narrowly avoiding a collision at (presumably) a level crossing on the Santa Fe railroad in Seligman, Arizona.
Used Cars (1982): A race against the clock to get the last of "a mile of cars" to a lot leads to a vehicle being involved in a near-miss at a level crossing.

Live Action TV

The Dukes of Hazzard: In at least one episode, the villians barely made it across a railroad crossing with a train coming, to escape pursuit by the Duke boys and the General Lee. Bo simply used a convenient ramp to jump over the train in eventually catching the baddies.
Operation:Livesaver: The public safety awareness campaign's "These are the next 60 seconds of your life ..." series of commercials often depicted the consequences of racing a train, always with deadly results. One common example showed a Volkswagen Cabriolet, filled with five teen-agers joyriding, speeding and trying to race an oncoming train to the crossing; needless to say, they didn't make it and the community where they lived was thrown into sudden and deep mourning.
Top Gear has used the format several times with Jeremy Clarkson in a car vs. James May and Richard Hammond riding the train. In Europe the train was the Eurostar and TGV, and in Japan it was the Shinkansen.

Video Games

In Megaman X4, Slash Beast shows up to the Traintop Battle by running parallel up to, then jumping onto the train car used as his boss room when X or Zero get to it
Piston Hondo does this in Punch-Out!! Wii in his backstory.
One of the robotic bosses of Contra Hard Corps and Contra: Shattered Soldier makes his entrance by outrunning the train you're on, pushes it to a stop, lifts the end of it, then climbs on top. This turns out to be a bad idea in the end- upon defeat, he falls backwards off the front of the train, and gets hit by it!
- And in Contra: Shattered Soldier, an Expy of said boss does the exact same thing, except that you're on a small train carriage which the boss lifts off the ground with ease.
Jude of Wild ARMs 4 does this while riding a bicycle. The bike eventually breaks from the strain.
The level "Wrong Side of the Tracks" in Grand Theft Auto: San Andreas involves you and Big Smoke trying to chase a train while on a dirt bike so that he can shoot the rival gang members atop the train. It's That One Level, due to the fact that the game never tells you that you need to be at least another train's width away from the train so that Big Smoke can hit them.

"All you had to do was follow the damn train, CJ!"

Western Animation

In the Road Runner cartoon "Zipping Along," the establishing scene features the bird zipping along a train, although he leaves the road and never attempts to beat the train to the crossing.
- The Road Runner's observation of safety is reprised in a later Operation:Lifesaver commercial aimed at children. In it, the Road Runner, despite his ability to put some extra speed in his already fast run, is aware of safety rules concerning railroad crossings and stops to allow a train to pass. Of course, Wile E. Coyote arrogantly doesn't, and he (once again) is crushed beneath another oncoming train.
The MGM cartoon One Cab's Family, starting around 5:15
In Warners' Streamlined Gretna Green, Junior the roadster tries to outrace a train, gets hit (naturally) and has to go the hospital/body shop; once he recovers he then goes and does it again, this time it's the train that gets the worst of it.

Real Life

The Blue Train Races were a series of famous match races between racing drivers and trains in the 1920s and 1930s.
There is a race in southwest Colorado called the Iron Horse Classic where cyclists race an old steam train 50 miles through mountainous territory. The train almost never wins.
There are plenty of stories about people in cars (or on bikes, or on foot) who try to beat trains to crossings. Most of them end up dead. Remember, when you race a train, if it's a tie, you lose.
Some UK heritage railways have organised 'race the train' events, with a designated route near the line. In this case the trains are slow enough that it's achievable.