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Or take the MRT (Mass Rapid Transport = Metro) : Red Line to "Marsiling station" (Attention: the border checkpoint is called Woodlands, don't get out at Woodlands station but in Marsiling which is closer).
From there take the bus 950 that takes you to JB. Then you can hitch out of customs just walking up the road. It is definitely illegal, but it is rare to be harassed by police for standing right on the freeway in Malaysia.
2019 edit:
Take the MRT from the airport (Changi Airport) from the Green Line and transfer to the Red Line, to woodlands station. You can take multiple buses to JB, just type into google maps "JB Sentral Mall" and you'll see a number of buses come up, they're pretty reasonable.
It's more likely that you're to be questioned by police in Singapore for hitchhiking, and get lots of curious stares, than if you do it in Singapore. Singaporeans have only heard of the concept of hitchhiking through movies and books, because the country takes literally 30 minutes to traverse from one end to the other, and due to the dense road usage, it's generally not heard of.
Malaysians have seen more in their time, no doubt!
=== Hitchhiking from Singapore ===
