Matplotlib legend, add items across columns instead of down

I can think of one possible way. You can order your legend items as you like. All you need to do is to switch the order so that it will give you the result you want.

import matplotlib.pyplot as plt
import numpy as np
import itertools

def flip(items, ncol):
    return itertools.chain(*[items[i::ncol] for i in range(ncol)])

x = np.arange(-2*np.pi, 2*np.pi, 0.1)
ax = plt.subplot(111)
ax.plot(x, np.sin(x), label="Sine")
ax.plot(x, np.cos(x), label="Cosine")
ax.plot(x, np.arctan(x), label="Inverse tan")

handles, labels = ax.get_legend_handles_labels()
plt.legend(flip(handles, 2), flip(labels, 2), loc=9, ncol=2)

plt.grid('on')
plt.show()